Commercial Real Estate Investing From A-Z

Steffany Boldrini
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Nov 20, 2025 • 24min

100% Bonus Depreciation & Other Tax Benefits in Real Estate

Can you take 100% bonus depreciation on parts of your property? What is the difference between accelerated depreciation and bonus depreciation? What are some other things you may now know to depreciate even more in real estate? Tom Brodie from CSSI shares his insights.Tom BrodieCSSI - Cost Segregation Services(713) 906-3710tom.brodie@cssiservices.comwww.CSSIServices.com/tom-brodie
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Nov 6, 2025 • 12min

How I Made 25% IRR on My Worst Investment!

How did I make money on my first and worst investment? I’m going to be breaking down my first and worst investment and how I ended up making money on it and getting a free storage facility even after closing the business for 2 years.Read this entire interview here: https://tinyurl.com/mr22f6mxTop lessons learned from this experience:- Don’t ever get into an asset class that you know nothing about without first going to industry specific events, building relationships, asking questions, and getting an advisor to help you analyze and purchase your first deal.- Buying portfolios can be a great thing, you get multiple properties at a discounted rate, and after you buy them, you split them up and sell a few at market price, while keeping the others.- This is not really related to car washes, but I have heard that the first offer you get is typically the highest offer you will get, and it turned out to be true in this case. When I decided to sell them while they were still open, we got an offer that was higher than the one that we ended up taking, but I turned it down because at that time the properties were not distressed and our sales price was based on actual NOI. However, it confirmed this theory that the first offer that you get is typically the highest offer you will get.- Work with a broker that exclusively sells that specific asset class, and follow up with them on a regular basis to make sure you and your properties are on top of their mind. I’m a believer in showing up and following up because people easily forget about you, whether you are selling or buying a property, you need to keep people accountable. This is not to say that the broker wasn’t working on them, but it was to keep reminding her that I was really interested in selling them. My follow ups were about once a month/once every other month.- There’s a known saying in real estate that “You make money when you buy”. And because I got these properties at a great price, and even though the deal was a complete failure, that is another reason why this worked out. Proving another real estate theory to be true.Three years after purchasing these properties I decided that it’s not worth my time to try to fix it, and that I’d put the car washes up for sale, and close them completely. Not knowing when I was going to be able to sell them. I decided to take the hit on the mortgage payments until I sold them because my time was not worth the time that I was spending trying to solve that problem. The mortgage payments were cheaper than my time. The car washes stayed closed for two full years. Last year I managed to sell one of them, and this year I sold the remaining two, two years after completely closing them. I hope that you can learn from my lessons learned, so that you don’t have to make the same mistakes that I made. To better investments!www.montecarlorei.com/investors
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Oct 23, 2025 • 20min

Why Are Car Washes a Great Investment? Why is Now a Good Time to Buy? What Should Investors Keep in Mind?

Why are car washes a great investment? What investors should keep in mind when buying car washes? Why now is the time to buy? Why have car washes grown in popularity? Melissa Croll, Associate Partner at Attlee Realty, shares her expertise.Car washes have been a hot topic with investors for the last few years, why are they a good investment?The popularity of car washes has definitely grown since I started. We began selling car washes because there was an influx of equipment orders. We were asked by an equipment operator to start doing site selection. In the beginning, we were looking for land, and that eventually led to what we do now—selling existing car washes and everything that comes with them.What’s really brought car washes to the forefront is the recurring memberships. Every city has its own weather challenges. Here in Dallas, for example, we sometimes get those random freezes that people might not know about. Other markets have a lot of rain. It depends on your market, but these recurring memberships allow somebody to sustain income even during the down times. You don’t need a sunny day to make an income if you play your cards right and build those memberships.Another reason is that car washes are low-labor businesses, which is part of why they’ve become so popular. With self-serves, for example, you have minimal staffing needs. Of course, you still need someone to pick up trash and ensure everything is working correctly, but not having to hire a large staff is very appealing to investors. The express tunnels need a lot fewer people than opening a restaurant or a retail store.What should investors keep in mind when buying car wash sites for building a car wash?It’s real estate 101: we need to consider our location. This is especially important in car washing, because you have to think about a car wash as an impulse buy. If I am driving down the road and there’s a car wash, I should stop. But if I can’t turn around or get to it, I’m probably not going to turn around and go back. Now, if it’s right there and I can easily get to it, I’m going to pull off and wash my car because it was an impulse buy.These are all things we look at: ingress, egress, and population. You want to make sure the area can support the car wash. How close is the competition? These are all considerations we take into account, even when we’re selling dirt. And whenever we’re working with somebody to rebuy a car wash, we go through all of this with them because, at the end of the day, we want our buyers to be successful. Hopefully, they’ll continue to buy more, and we love seeing them succeed.Why is right now a good time to buy car washes?I will say there’s a sense of urgency right now for many people. As you know, this year they passed the Big, Beautiful Bill, and this is huge for our industry. We’re back to 100% depreciation, and you can take advantage of cost segregation. What that means is you can write off equipment and similar items, which can save significantly. I literally have people coming to me now in October trying to close before December 31, saying, “I need to close so that I can get some tax write-offs.”For many reasons, I’d say there’s a sense of urgency right now. If you want to take advantage of buying a car wash and benefiting from that tax law, you need to do it now because a car wash deal can take 30 to 90 days to close, so we’re really at that point where, if you’re going to get it done, you need to be going under contract now.Melissa Crollmelissa@attleerealty.comhttps://www.instagram.com/carwashprincessmelissa/www.carwashtraders.comJoin our investor list here: https://montecarlorei.com/investors/
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Oct 2, 2025 • 21min

Capital Crunch or Capital Flow? The State of Syndications & The Real Estate Market

What is the state of raising funds for real estate syndications? What is the state of the market today? Mike Morawski, a seasoned investor and syndicator, shares his insights.Previous interview with Mike: https://tinyurl.com/3hjx8j3dhttps://tinyurl.com/vb6yyzznMike Morawskimike@mikemorawski.comhttps://www.linkedin.com/in/michael-morawski/Subscribe to our investor list here: https://montecarlorei.com/investors/
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Sep 4, 2025 • 20min

Lessons Learned on Our First Deal in 2025

Today we are talking about a deal we recently raised for, mostly so you can understand some of the things that happen behind the scenes and why we decided to have this be our first syndication for 2025.Read this episode here: https://tinyurl.com/2km2c2k9Why did it pass our test besides the fact that these partners have a great track record and having exited 4 deals with them?1. Low vacancy. There is a shortage of small bay industrial in the Phoenix market, people have been building large bay industrial. For the small tenants that need a smaller space, the available inventory is very low.2. Leases expiring and below market. A lot of the tenants had their lease expiring during our ownership, and the vast majority is below market, one of the largest tenants in the property with the biggest rent upside, already decided to not renew. We underwrote them not renewing a year from now, and they are significantly below market.3. IG Leases. All of the tenants except one are on industrial gross (IG) leases. We are converting all of the tenants to NNN leases. This will also increase the bottom line for our investors.4. Prohibited cost to build. Besides the market having very low vacancy, the vast majority of tenants being between 30 to 70% below market, and the leases expiring in the next 24 months, small bay industrial is cost prohibited to build. It costs more to build than the rents that you’re going to get. We are purchasing the property at a significant discount to replacement cost. The property was built in 1999 and it looks really good.5. Location. The property has freeway visibility and is right next to the freeway exit.6. Market. Phoenix is a phenomenal market. It has a 16% population growth since 2010, a job growth of 45 to 50% since 2010. The personal income tax is very low at 2.5%. They’re exploding in terms of plants, campuses, and jobs being created in the area. There is a $65 billion chip plant being created next to the property. There is a $20 billion Intel expansion. These are all creating jobs, which is always a great sign of a phenomenal market to be in.Final ThoughtsThe raise took a little bit longer than what we thought it was going to take. We did not finish the entire raise and still have a couple million to go, however, we did manage to close on the property and the couple million that we have to go is mainly for reserves, so that still needs to be finalized.Commercial Real Estate Tips Learned Recently:Turn expense into income: e.g., rent dumpster out.You can open a Senior Living home in any state if one tenant has a disability due to the ADA / Fair Housing Act.Always over-raise in case investors don’t send funds.If a deal blows up, attorney often refunds fees (to keep you as a client).When you refinance, you don’t pay taxes. This means you can cash out of a property, or get a line of credit, and buy another property without paying taxes on that down payment. Make sure you are comfortable with the LTV’s when you cash out.Interest rates are always negotiable, you can get ~0.25% interest rate break if you open a checking/savings with lender.When developing a property from the ground up, always assume that the piece of land has all of these: endangered species, wetlands, easements, utility issues, trees – until proven otherwise. This means you need to get all of these reports and surveys done (amongst many other things)) before purchasing a piece of land for development.Join our investor club here: https://montecarlorei.com/investors/
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Jul 17, 2025 • 25min

SEC Traps & GP/LP Structures for Infinite Cashflow

With regards to SEC exemptions and compliance, what are some of the common mistakes that syndicators make? What are potential consequences if the SEC finds out you paid a GP to raise capital? How would you structure a deal for the GP's and LP's to hold real estate forever and get infinite cashflow?  What are some of the legal challenges and opportunities in real estate investing today? Jonathan Tavares, Managing Partner of Premier Law Group shares his knowledgeAlso some great news for raising funds: an investor can now be considered accredited if they invest 200k or more in the offering!Jonathan Tavares(508) 212-1193jonathan@plglp.comwww.premierlawgroup.netJoin our investor club here: https://montecarlorei.com/investors/
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Jul 3, 2025 • 26min

What Are The Pros And Cons of Office, Retail, and Industrial? How To Overcome Fear in Investing?

What are the pros and cons of office, retail, and industrial? What should your real estate agent do for you as a buyer? How to get over fear in real estate investing? Trinity (Trent) Herrera, commercial director and real estate consultant of Black Tie Real Estate, shares his insights.Read the entire episode here: https://tinyurl.com/4dzzaartThe pros and cons of officeProfessionals need an office, so it's a staple in downtown areas. A stabilized office can fetch a premium. Some of the most expensive and impressive buildings in the world are office buildings. The cons are that we have a lot of office vacancies, and we have more work-from-home opportunities post-COVID, which completely turned the office upside down in some cities, counties, and towns. We have many cities with a lot of impending office vacancies. However, as another pro, I'm hearing about a lot of discussion about multifamily conversions and turning these office buildings into high-quality multifamily units, which also serve a need. The singular scariest thing about offices as products is being left responsible for the building. If it's 30% vacant or more, that's the single most frightening thing.The pros and cons of retailThe cons we're talking about here are the opportunities. What scares us are often the opportunities. While the scariest part of an office could be holding the bag, paying the property taxes on a building that's assessed for what it's worth is a little frightening. But when you lease it, when you hold and plan correctly, you have a good team, and you have it for 10 cents on the dollar because it's been vacant, it's a whole different story.If you want to be extremely safe, you'll put your money in a savings account. If you want a slightly higher risk, you put in a retail triple-net tenant that will give you the mailbox money, but it's at 5%. It goes for everything.The pros and cons of industrialThe biggest pro for me is that there has been a recent focus on the domestic industry. We have a lot of local infrastructure being built around US-based industries, such as manufacturing, warehousing, new Amazon distribution, data centers, and OpenAI Stargate. A lot of money is being invested in it. There is this sentiment that each country should be able to manufacture its products, and I think we're sensing that now. Hopefully, we continue to see this trend.Americans love buying things. The same reason that retail works is why the industrial works. So much industry is built around shipping products, getting them from A to B, warehousing for Amazon, etc. Even if people stop going to the retail store, Amazon is always going to need warehouses. There will be many companies providing other forms of distribution and accessory services to Amazon. As long as Americans love buying stuff online or in person, the industry will likely remain strong.And then there's opportunity. There are a lot of small towns, especially here in Texas, that have 100 to 300,000 people, where you can buy quality industrial for 30 dollars a foot. If you can tolerate a hold and lease it up in a year or two, those deals can be had all day, and there are lots of more stabilized national credit tenant deals to be had. There are all sorts of things that can be found with a propensity for appreciation.Trent Herreratrinity@blacktie-re.com Join our investor club here: https://montecarlorei.com/investors/
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Jun 19, 2025 • 21min

The CRE Playbook: Goals, Asset Classes & Agent Roles

What should be your acquisition targets and goals as an investor? What are the pros and cons of different asset classes? What should your real estate agent do for you and what should you do as an operator? Trinity (Trent) Herrera, commercial director and real estate consultant of Black Tie Real Estate, shares his knowledge.Read the interview here: https://tinyurl.com/54p9jcvmHow should people decide their acquisition targets?This is incredibly unique to each person. What's your appetite? Is it residential or commercial real estate? Let's assume it's commercial real estate. Each economist, economics professor, person who studies economics, and person who works in finance or retail is part of a cycle. Every city, block, town, county, state, and even country is in a different cycle of everything all the time. It is chaos.One of my favorite topics to talk about is the concept of the three-body problem. When you have one item, it is easy to predict what that item will do. It could be a planet, a financial entity, or a person. When you have one variable, it's very easy to calculate. When you have two variables interacting with each other, it starts to get a little harder. But when you have three or more, you start to reach an incalculable level of complexity. When scientists study planet orbits or ask whether this asteroid is going to hit us, they're always calculating a three-body problem. And we have this with real estate in so many ways. It is this chaotic complex, constantly orbiting, always spinning, and shifting off its orbit. It is truly the epitome of a three-body problem, in the sense that it is so vastly complex. It's extremely hard to time.Most brokers don't bring the math with them.No, they don't. And it's a big gripe of mine because I work with my peers in the real estate world every day, and as soon as you get to any level of sophistication in commercial real estate, you're crunching numbers pretty hardcore. When you have a fiduciary responsibility to somebody to protect their wealth and their money and make money for them, how can you do that if you can't deeply understand the math? It's one of my cardinal sins in the commercial real estate practice. As an agent, you should understand math and be able to explain it to everybody.And my wrap-up on acquisitions: find a good partner, stay away from sizzle and hot. You want to be cold in your thinking and logical, knowing your asset types and your "why." This is partly what you're looking to your sponsor for, and part of the relationship you have with your sponsor. The appetite your sponsor has will have a bearing. If you're doing LP or investments like that, then you're going to want to work with a sponsor who has deals that you like.Trent Herreratrinity@blacktie-re.com Join our investor club here: www.montecarlorei.com/investors
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Jun 5, 2025 • 18min

Protecting Your Investment: Vetting Syndicators & Operators the Right Way

How to make sure a syndicator/operator cares about your money as an investor, what can you do to mitigate the risk of investing with a bad operator? Trinity (Trent) Herrera, commercial director and real estate consultant of Black Tie Real Estate, shares his knowledge.Read the entire episode here: https://tinyurl.com/mr4ces9cHow can a passive investor know that a syndicator/operator cares about their money?We've all looked at deals that, at the surface, the sponsor looked great, and everything was above board, and the yield was what we wanted, and it was our appetite. And something happens. And to some degree, I think that you can never, 100%, insulate yourself from a bad egg, but there are signs. We have this term in the industry, commission breath, that's always a number one red flag. Someone with a servant mindset is not going to have commission breath at all. There's no sizzle in that industry of building generational wealth, the sizzle is, we're going to build generational wealth using math and fundamentals. But when there's too much sizzle, that's a red flag.The biggest single indicator is the math and the story, and the history track record. When you have a target of an asset type or class that you're comfortable with, and when you have a track record, when you have some under your belt, it's easier to see when something doesn't look or feel the way it should in that industry. I guess I will answer that by saying the single biggest defense is sophistication and experience, and maybe even leveraging your friends, there have certainly been friends that have saved me from bad investments, just from a second look and talking through a deal.We're talking about the foundation of what makes a syndication or an investment successful, Underwriting is no joke; it's 75% of what makes a syndication work. My best clients, my best investors, all understand underwriting, and if they don't, they've hired me to help them understand it, and to walk them through it so that they can see what I'm seeing. There are so many ways that you can look at a property wrong. And I also believe that not one person should look at a property. There should be a multitude of people and aspects looking at a property, opining and giving valid, good criticism and feedback. My number one tip when it comes to foundations is to dive into underwriting and do your best to understand each deal; it takes years, and even then, there are still deals that you see and you struggle. The underwriting in the math is where you'll see if the deal is truly viable for you or not. And that goes along with the risk management side and accreditation.Each one of us has a very different life. We all live such different lives, and we all have different amounts of kids and cars and mortgages and investments, and so we all have these tolerances and knowing what those are for you through the eyes of someone like you or I, who's been doing this for a long time, is important, understanding the level you should be playing at. How much is too big a bite off for you? How are you accredited? What's your accreditation level? Those things are all guardrails that are in place to help each investor make good decisions. Each style of offering that is done is styled differently to either accept less of a wealthy and sophisticated base or not, through your underwriting and through your understanding of your life and your position, not biting off more than you can chew, and only investing money that you can tolerate losing.Trent Herreratrinity@blacktie-re.com Join our investor club here https://montecarlorei.com/investors/
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May 21, 2025 • 22min

Syndications & Funds: Behind the Deal

What is the state of syndications today? How to structure a syndication for protection purposes? Major differences between funds vs syndications and why are funds popular today? Jonathan Tavares, Managing Partner at Premier Law Group, shares his insights. Read the entire interview here: https://tinyurl.com/25hhhjsfWhat is the state of the market today? What are the IRRs looking like? Are you seeing more or fewer deals come across your desk?There has been a shift to funds in the last 6-8 mos. Traditionally, especially during COVID, a lot of clients were doing a lot of multifamily syndication. Now, granted, that's been a piece that we focused on for a long time. A lot of our clients are heavily involved in the multifamily space, but with increasing interest rates over 22 and various other factors, property taxes throughout many counties and throughout the country, going up very quickly, as well as insurance and specific markets. We have a lot of clients in various markets in Texas that have just gone crazy, places like Houston or Florida, where insurance rates have skyrocketed. It's presented some challenges for some of our clients. Instead of seeing just a straight deal with a certain percentage of debt somewhere around 70- 80%, a lot of times, there's a lot of creative financing going on to make up for that debt piece that may not be there or where those percentages of debt to purchase price may be a little bit lower than what a lot of clients were used to before.You see a lot of preferred equity. We've seen clients building out structures where, in essence, they're providing almost a debt structure to their investors too, to create a sort of debt piece as well as an equity piece in their raises. We've seen a lot of clients create funds and use their funds to come in for part of the debt piece for specific projects as well.Depending on the asset type, and I'll specifically exclude development projects, we're seeing a lot of target IRRs between 15 and 20% generally.Where do all the LLCs go for a syndication so that everyone is protected as much as they can possibly be?There's all sorts of different structures that you might use to set up a syndication or a fund and for different reasons, for tax reasons, for asset protection reasons, etc. A typical syndication structure is going to include a syndication entity, and that's typically known as the issuer entity, that's the entity that's selling securities.Why does the SEC care about what I'm doing if I'm raising capital to go buy real estate? The Supreme Court came up with a test that's called the Howie test. The SEC does an analysis to determine if you were selling securities or not, and essentially boils down to the four main tenets of the Howie test:1) Is an investor investing money? Typically, the answer is yes.2) Are they expecting some sort of return on profits? And usually the answer is yes.3) Whether the efforts are generated by someone other than the person who's investing, like some sort of promoter, or in the space we call a sponsor. In these deals, a sponsor where a GP that is raising the capital from investors. The investors are passive in the deal. 4) A common enterprise is if the investors are pooling together capital through the efforts of the GP to buy some sort of underlying investments. That's typically going to be real estate.Jonathan Tavares(508) 212-1193jonathan@plglp.comwww.premierlawgroup.netJoin our investor list at https://montecarlorei.com/investors/

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