Scaling to 100+ STR Units Without Compromising Quality

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What happens when a short-term rental operator scales past 100 units in a highly seasonal market and still refuses to compromise on quality?

In this episode of Get Paid For Your Pad, Kaye Putnam (Head of Marketing at Freewyld and Freewyld Foundry) sits down with Troy Daily, CEO of Elevated Stays, to unpack the real operational, leadership, and systems work behind scaling a 100+ unit STR portfolio in Traverse City. Troy shares how his business grew from a small operation into a professional short-term rental company managing over 100 units, while maintaining brand standards, guest experience, and owner alignment.

Whether you are managing 20 listings or planning to scale toward 50 or 100+, this episode gives you a grounded look at what actually breaks when STR portfolios grow and what needs to be built to support that growth. Troy explains why systems, people, and quality controls matter more than rapid acquisition, especially in seasonal markets with extreme occupancy swings.

You will discover:

• How to scale a 100+ unit STR portfolio without losing quality

• Why systems become non-negotiable as STR operations grow

• How leadership responsibilities change when scaling past 50 units

• Why in-house housekeeping and laundry improved operational control

• How quality standards directly impact ADR and repeat bookings

• Why owner alignment is critical when managing large STR portfolios

• How to approach growth in highly seasonal STR markets

• What to consider when evaluating new acquisition opportunities

Kaye and Troy also explore the reality of renovating older properties to meet modern guest expectations, including turning a 150-year-old building into a boutique-style STR asset. They discuss investing over $700,000 in renovations, why not every property belongs in a growing portfolio, and how splitting housekeeping and operations roles created clarity and accountability. The conversation also covers planning during low season, managing 90% summer occupancy and 10% winter occupancy, and why experience-driven amenities can elevate both revenue and brand perception.

💡 Topics Covered:

• Scaling short-term rental portfolios past 100 units

• STR operations, systems, and quality control

• Leadership and team structure for growing STR businesses

• In-house housekeeping and laundry operations

• Owner relations and portfolio alignment

• Seasonal occupancy planning and off-season strategy

• Renovating legacy properties for STR performance

• Guest experience, amenities, and ADR growth

🔗 Relevant Links:

Learn more about Freewyld Foundry → https://www.freewyldfoundry.com

Follow Kaye Putnam → https://www.linkedin.com/in/kayeputnam

Follow Freewyld Foundry → https://www.linkedin.com/company/freewyldfoundry

Keywords:

short-term rentals, STR scaling, 100+ STR units, STR operations, property management, seasonal markets, guest experience, quality control, STR systems, boutique short-term rentals, Airbnb portfolio, vacation rentals, STR leadership, owner relations, ADR optimization, portfolio growth, professional hosting, Freewyld, Freewyld Foundry, Get Paid For Your Pad

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