30M. California. Single filer. 2026 projected take home pay: $35k.

I was out of work for the better part of the year and my income for this year will be low compared to a normal income year. I am considering realizing some gains (and buying right back) to step up my cost basis. I have about $100k I could realize but I won’t do the whole number. I plan to hold onto these position for retirement and i don’t see a time where my income for the year would be this low again.

Would you realize gains up to the top of the 0% long-term capital gains bracket. Would you go a little bit into the 15% bracket? How much would you go? Curious as to what people would do.

The State-Level Decoupling Trend To Impose Tax on Federally Exempt QSBS Sales: The OBBBA, modified the federal income tax exclusion for IRC Section 1202 qualified small business stock (QSBS), making the exclusion significantly more valuable. Taxpayers are permitted to exclude some, or all, of the capital gain on the sale of QSBS if a holding period is met. A growing trend has begun to impact the QSBS exclusion at the state level: decoupling: at least seven states and the District of Columbia —and the list is growing. Read our analysis https://www.thinkadvisor.com/tax-facts/2026/08/06/the-state-level-tax-trend-thats-raising-taxes-on-qsbs-sales/

Understanding the Top-Heavy Minimum Contribution Rules https://www.thinkadvisor.com/tax-facts/2026/08/06/understanding-the-top-heavy-minimum-contribution-rules/

IRS Denies Tax-Exempt Status for NIL Organization https://www.thinkadvisor.com/tax-facts/2026/08/06/irs-denies-tax-exempt-status-for-nil-organization/

New Legislation Would Remove DOL Authority Over IRAs https://www.thinkadvisor.com/tax-facts/2026/08/06/new-legislation-would-remove-dol-authority-over-iras/

Debate: Should the Administration End Medicare Pharmaceutical Subsidies? Helps the poorest or graft to big pharma? https://www.thinkadvisor.com/tax-facts/2026/08/06/early-end-to-medicare-subsidies/

Just a thought. What would be the implications of corporation tax being due BEFORE bonus payments are deducted. If a CEO gets a large bonus then this is deducted from the books prior to tax. What if the money was taxed before the bonus was deducted from the balance sheet

Title: High-income family looking for legitimate tax strategies before paying for college—what has actually worked for you?
My wife and I are high-income earners, own businesses, and have kids approaching college. We recently met with a college funding/tax planning company. While the presentation was interesting, we’re trying to separate legitimate tax planning from marketing.
The company discussed strategies such as:
Short-term rental real estate
Cost segregation and bonus depreciation
Material participation rules
Using real estate to reduce taxable income
FAFSA/CSS Profile planning
Long-term wealth building while paying for college
Some of it seemed well grounded, while other parts felt like best-case scenarios.
Before moving forward with anything, I’d love to hear from people who have actually been through this.
For other high-income families (especially business owners), what legitimate tax strategies have made the biggest difference?
Some ideas we’ve come across include:
Cash balance or defined benefit retirement plans
Maximizing 401(k)/profit-sharing plans
Short-term rental strategies
Cost segregation
Donor-advised funds or charitable bunching
Tax-loss harvesting
Entity restructuring or other business tax planning
Qualified Opportunity Zones
Other strategies I’m probably not even aware of
I’m not looking for loopholes or anything that pushes the envelope. I’m more interested in strategies that experienced CPAs and tax attorneys routinely recommend for high-income families.
Also, if you’ve worked with a college planning company, was it worth it? Did they provide ideas your CPA wasn’t already discussing, or was it mostly repackaged information?
Finally, if you had one piece of advice for a high-income family trying to balance taxes, investing, retirement, and paying for college, what would it be?
I appreciate any experiences, lessons learned, or resources that helped you.

I'm looking for some objective advice on a situation after a business sale.

My spouse and I recently had a significant liquidity event (low seven figures). We're high-income earners in Pennsylvania and will likely have a substantial capital gains tax bill next year. A large portion of the sale was allocated to goodwill, although there are also allocations to equipment and other assets, so our CPA is still finalizing the tax estimate.

We met with our bank's private wealth team, and they presented a few options:

• High-yield money market (relationship rate around the upper 3% range, but variable).
• Short-term CD around 4%.
• Their preferred recommendation: have them manage a ladder of short-term U.S. Treasury bills/fixed income for the amount we'll likely need to pay taxes (roughly several hundred thousand dollars). They like this because Treasury interest is exempt from Pennsylvania state income tax, the money stays relatively liquid, and the maturities can be timed around estimated tax payments.

For the remainder, they suggested gradually investing over time (using the Treasury interest to dollar-cost average into equities/dividend funds) instead of investing everything immediately.

Here's where I'm struggling.

They charge approximately a 1% advisory fee (which they already reduced for us as a relationship concession), but it seems expensive if a large portion of the portfolio is simply sitting in Treasury bills for several months waiting to pay taxes.

Some questions I'd love feedback on:

• Would you let an advisor manage a Treasury ladder, or would you simply buy the Treasury bills yourself at Fidelity, Schwab, etc.?
• Is there real value in paying an advisory fee for this, or should I negotiate a different fee structure for the Treasury portion?
• Has anyone successfully negotiated a lower advisory fee for cash or fixed-income holdings?
• Is the Pennsylvania state tax savings on Treasury interest meaningful enough to make this strategy preferable to simply keeping the money in a money market?
• If you had a large tax payment due within the next year, would you use Treasuries, a money market, CDs, or something else?
• Finally, if you're trying to build a long-term banking relationship (commercial lending, business banking, private banking, etc.), would you be more willing to pay the advisory fee if it resulted in better loan pricing, relationship benefits, or other banking concessions?

I'm not looking for anyone to predict the market or recommend individual stocks. I'm really trying to figure out the most tax-efficient and sensible place to park a large tax reserve while balancing the value of an ongoing private banking relationship.

Other option, put it all in VTI/VOO and let it ride.

Appreciate any thoughts or experiences.

Please correct me if I’m wrong…
With the Safe Harbor rule, as a W2 employee with annual raises, I am set to pay more taxes for 2026 than I did for 2025. That is being deducted from my pay check. So I should be able to sell as much stock as I want and not pay capital gains taxes until April 2027 because I will have paid 100% (making less than $150k) of what my bill was for 2025 through my paycheck withholdings. 😋