Sell Long-Term Gains, Check Cost-Basis Method

#676: Ally:How can I optimize my asset allocation and Roth contributions now that I’m over $1 million in assets?

I’m 45, single, never married, with about $1.2 million in assets. Roughly $100,000 is in stocks, which might scare some people.

Here’s my breakdown:

• Vanguard brokerage account: VTSAX $132,000, ISCV $5,000, VOO $5,000
• Vanguard Rollover IRA: VTSAX $65,000, IVV $25,000, VOO $62,000
• Vanguard Roth IRA: VTSAX $228,000, ISCV $6,000
• Pre-tax 401(k): Active stock fund $218,000 (0.01% expense ratio), Equity dividend fund $55,000 (0.01% expense ratio)
• Russell 1000: $270,000 (0% expense ratio)
• HSA: $9,000 in the Russell 1000 and Russell 2000
• ESPP: $90,000
• Savings account: $12,000

I view my brokerage accounts as savings, where I can sell assets if I need cash, as well as sell my company shares.

My questions: How far am I from the efficient frontier? How efficient is my asset allocation? I’ve mostly been a “VTSAX and chill” type. If I rebalance, what’s the best way to do it without incurring taxes?

Next year, I’ll make more than $150,000, even after contributing $24,500 to my pre-tax 401(k) in 2026. Can I still do a backdoor Roth, given that I already have an IRA balance? I was told it could be complicated. Am I out of luck investing in a Roth next year?

Also, should I roll over my 401(k) into my existing Rollover IRA to gain more investment options, even though the 401(k) fees are very low?

I’ve reached over $1 million in assets, but I’m not confident my first million was invested efficiently. I want to correct it before reaching my next million.

Emma: Can We Split a Dependent’s Tax Status Midyear to Maximize Health Insurance Subsidies?

We’re a family of four with two adults and two children, ages 15 and 21. Our 21-year-old is a full-time university student and is expected to graduate in May 2026. The hope is that she’ll secure a full-time job after graduation.

Our health care broker told us that we could claim her as a dependent for half of the year and then have her claim herself for the second half. According to the broker, this would allow her to stay on our health insurance and help us qualify for a larger premium subsidy.

Is it actually possible to split a dependent’s tax status this way within a single year, or is this a misunderstanding?

Anonymous: Is It Wise to Hold Some Investments Outside the U.S. for Geopolitical Diversification?

I’ve always believed that “this time isn’t different,” but lately I’m feeling uneasy.

I’m increasingly concerned about what seems like a slow erosion of institutional trust in the U.S., especially regarding agencies and structures that support our financial system. From leadership changes at key government institutions to growing political influence over economic policy, I’m starting to wonder if it’s prudent to hold a small portion of assets physically and legally outside the U.S.

I’m not talking about exotic offshore schemes. I mean legitimate ways to invest in broad index funds or ETFs through a brokerage account based abroad—as a form of geopolitical diversification and personal contingency planning. I’d love to hear your perspective.

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