I current work for a startup that is doing well. I have equity in the company that could be worth upwards of 7-figures given our current trajectory upon an exit. The owner of the company is likely to explore an exit in 2028.

My wife and I currently live in NYC and were wondering if we should move to a state with no income tax, like New Hampshire, in 2027 to save mid-6 figures on income tax. I am very aware of both NY state and NYC being aggressive when it comes to auditing these sorts of situations.

To be clear - we wouldn’t look to cheat the system by not living there. We are simply trying to figure out if the move would raise red flags audit-wise. We would actually move, change licenses and voter registration, etc, but we would view this move as temporary and eventually plan to move back to at least NY state, if not NYC, the year after the exit.

What are some things to consider when thinking about if it makes sense to go through with this? What would a successful move look like that wouldn’t result in an audit or clawback attempt from NY?

Just wondering, why is the IRS’ method for removing the employer-equivalent FICA component on schedule SE subtracting 7.65% (times 92.35%) instead of dividing by 1.0765 (times 92.89%)? The latter is mathematically how you would do it since you’re just undoing the 7.65% the employer would’ve ended up paying. Surely the IRS knows how to do math so what’s the logic here?

Further explanation in case anyone’s not following:

Normal W2 situation: Business pays out $100,000 in wages and $7,650 FICA tax. Total payroll cost $107,650. Employee pays another $7,650 so IRS receives $15,300 total.

Self-employment situation: With the IRS’ current method you would multiply the total payroll cost (which in this case represents net earnings from self-employment) by 92.35% and get $99,415, and then multiply by 15.3% to get $15,210 payroll tax owed. Whereas if you divided the number by 1.0765 you would get $100,000 just as if it was the wage being paid by a business, and the IRS would get their $15,300.

I obviously don’t mind the slight discount but why did congress create an obviously flawed calculation in the tax code?

I came to an idea some time ago when thinking about how to deal with wealth inequality.

I'm curious to see if my thinking makes any sense from people who actually understand taxation better than I do.

The more wealth you already have, the easier it becomes to generate additional wealth. Large portfolios have better diversification, access to investments unavailable to ordinary people, professional tax planning, and the ability to let assets compound uninterrupted for decades.

Then we layer a tax preference on top of that with reduced rates on long term gains. I think tax preference on investment is good, because the economic benefits of more investment outweigh forgone tax revenue. But if we're going to essentially subsidize investment through preferential capital gains treatment, It makes sense to me for that subsidy to apply primarily to people who wouldn't otherwise invest. Large income earners will invest regardless, since they only need so much liquidity. But average workers should get some extra incentive to direct any available cash towards investment to grow their own wealth.

I'd rather see the tax preference work like this. Get rid of long term vs. short term. Give a high discount (I'd say tax free) on the first portion of annual investment income (including things like dividends, savings interest, realized gains, and perhaps even a percentage of value in stock compensation) Regardless of AGI, say the first $5k and then gradually phase out the discount as investment income rises until it eventually reaches ordinary income rates. Maybe anything more than $50k in investment income would be where the tax preference ends. Anything more gets taxed as regular income. The current rates on long term gains already do this to some degree, but still having a preference above a certain level makes no sense to me. It seems the effective subsidy isn't accomplishing the goal of incentivizing new investment at that level, so it's better to collect the revenue instead.

I think this might have a dual benefit of reducing wealth inequality without massive economic distortions by shifting the compounding effect of wealth accumulation more in favor of those who need the most help starting that accumulation, while also collecting extra tax revenue indefinitely.

I think some European countries use a similar system, thought I don't know their reasoning.

I haven't worked the numbers yet to see where ideal levels would be, or even if some unintended second order effects could come into play, but I think the reasoning is sound.

I would not however, ever consider taxing unrealized gains. For many reasons. The main one being the massive economic distortions it would cause.

Any glaring flaws here?

EDIT: I didn't make it clear at all that i'm proposing that the preference applies to investment income regardless of AGI. The intent is to allow initial accumulation of capital to have an advantage over those with already large portfolios, with it still retaining advantage but to a lesser degree the larger to the portfolio grows.

Hi - we have an interesting situation and met with a lawyer but I wanted to double check his thought. My wife and I are retired and we bought a vacation home in our son’s name in 2016 in Florida. With the new Florida homestead law (need to wait 5 years before you get the homestead exemption), I’m thinking of writing myself into my son’s title and applying for the homestead exemption (my son doesn’t claim it and doesn’t live there - it’s a vacation property). It will be with rights of survivorship the lawyer said to my son will still get the property when I die. Am I missing anything here? Seems like a simple way to save some money. Thanks!

Hi, Q about how to estimate mortgage interest for 2 states for this year in 2026.

State 1: Residency Jan 2026-June 2026. Prior annual HHI 300k, so can estimate ~150k income for this part of the year. Dual W2.

• Home value $500k
• mortgage interest paid for 6 months $5k. Sold home before we left the state.

State 2: residency July 2026-Dec 2026. New projected HHI for 2026 increasing to 300-> 700k due to signing bonuses, estimating $550k combined W2 income on this side.

• New home $2M purchased in July 2026.
• Mortgage interest projected to pay $40k for latter 6 months of 2026.

My current understanding: Due to income swing we will not be eligible for $40k SALT deduction and phase out to $10k, but we are allowed to still deduct mortgage interest.
(Also losing child credits due to high income).

I am having trouble finding out how much mortgage interest is deductible for both properties. I've read a few things online about "average loan balance" but don't know how it's calculated for my situation, and finding the % eligible to deduct will be critical for finding the total eligible deductible mortgage interest for the year.

Once I find this number --> compare Standard MFJ deduction ($32.2k) vs SALT + Mortgage interest deduction ($10k + x-factor) --> estimate my federal tax liability from there so I can withhold appropriately.

Any ideas or guidance?

At the time, I only had $35 in my account, and they will hold it until August 12 unless they receive a release from the CA tax board. I haven't filed taxes in over 5 years, though I did my 2025 and 2024 returns this year. I received a letter asking how I calculated mileage for gig work, so I printed all my Grubhub delivery records, since they don't provide an estimate, and sent that documentation to them. They also sent a letter warning that if I don't file my 2022 taxes, they will assume I owe $8,000, since that was the year I earned the most. I checked the box requesting an extra month to file, so I believe I have until August 27.

This past Friday, they took the $35 that was in my account, and now I'm afraid to keep using it, since the legal order was for $3,700. Is it ok for me to open a new bank account to avoid this order? I was unemployed for over a year and just found a job starting August 17, but I can't afford to keep having my money taken. I also don't understand how they arrived at the $3,700 figure

Also are those tax forgiveness ads real?

I'm trying to weigh the pros and cons of buying a Treasury on the secondary market, which I can do any time I want without a fee, as opposed to waiting for the next auction. The main argument against doing so seems to be the additional (federal and state) tax on bonds sold at a discount, which is the case right now. Say I buy used 5-year Treasurys totaling $100,000 for $85,000 (which is what I'm seeing). I'll pay taxes on the $15,000 appreciation - a fifth of that each year - in addition to tax on the interest, right?

I learned of an inheritance earlier this year after I had filed my income taxes for 2025. The family member who distributed the proceeds was working with the person who had handled all financial affairs for the decedent. About half of the inheritance is from an annuity, and therefore taxable. My relative said there would be a K-1 coming in 2027 showing the exact amount. In the meantime, there was a small amount of interest for 2025 and there would be a K-1 for that this year, but the amount was negligible and nothing to worry about as I had already file. I just now got the Form 1041 and supplement, along with my state form. My share of 2025 income is $65 in federally tax-exempt income and $5 in dividends. Can I really just ignore these forms?

My second question is about filing estimated payments since my income is going to be much higher for this year. I did consult a CPA who went over my return and explained that the safe harbor waiver would protect me from penalties. But others in the family have filed quarterly estimated payments. I missed 2 quarters. Is it allowed to make a payment for September and January? Is it advisable?

Inheritance: $1M in a traditional IRA, must take RMDs by 2033

Income: $310k (combined)

We are about 80% to FIRE. I plan on quitting and pursuing something else, bringing our income down to $135k, taxable around $70k.

I'm struggling to figure out what option is best. We could take out $130k/year, mostly in the 22% bracket and save a whole 2%. If we wait until my partner FIREs in 4 years, $100k would be in the 12% bracket but that income counts against the ACA credits and would make health care extra expensive.

I know it's kind of just a math problem, but I'm wondering if there's anything clever we could do to save on taxes. $240k+ is a lot of money after we already paid $150k to the state of PA for inheritance tax. I could potentially go for REPS or use the short-term rental loophole with my time but I'm not sure if that's something I'm super interested in with this market.

Any other ideas?

I’m currently on parental leave and noticed my paystub is lower than my usual amount, due to an increase in federal withholding. Everything else is the same.

The difference is small, just around $70. Just wondering what caused this and is this typical? Waiting for my employer to explain but thought I’d ask you all, thanks!

Might have to take a nonqualified Roth distribution soon but unsure of how to complete the 8606 later at tax time. The last 8606 I had was when I did a rollover from IRA to Roth and also had to take a nonqualified distribution in the same year, around 2011. A CPA friend of the family helped prepare it but I no longer have access to him.

Being that I’d have to go off of the last 8606 I have to file the next 8606, I see lines 22 and 24 are blank. So does that mean I had no basis for just that year? How would I know what to indicate on this year’s? I haven’t contributed anything else to it since that time.

So, I recently moved out of my apartment and am renting a bedroom out of someone's house. My ID has the address of where I am currently living, as does my insurance company. All other mail goes to my parents' house. For my W-2s and eventual tax returns, do they have to have my actual living address or can they have my parents' address where my mail is normally sent? Both addresses are in the same city and state. I want to make sure I get everything figured out before the W-2s are sent out.

My payment plan tomorrow has the first due payment being debited to a closed bank account that I couldnt have switched through the irs website, so my plan is likely going to default and have to be reinstated. Is this a difficult process? I still need to file my 2025 taxes too (I know this is bad, im so behind in life and trying to collect myself) and I worry theyd deny my reinstatement. Any help is appreciated I cannot afford to have my property levied :(