14 Could you explain more about this "step-up in basis" for inherited annuities? I thought that only applied to things like stocks and real estate, not annuities. Does it depend on when the original owner passed away?

20 The step-up in basis rules are complicated for annuities and depends on several factors. Generally, annuities don't receive the same full step-up in basis that other inherited assets might get. With annuities, what typically happens is that the income tax treatment passes to the beneficiary. So the taxable portion is still generally the difference between what was paid into the annuity (the cost basis) and its value at distribution. The step-up that can sometimes apply relates to the value at the date of death versus the original purchase price, but this varies based on how the annuity was structured and when the death occurred.

17 I tried that first actually! The customer service rep I spoke with just kept repeating that they "cannot provide tax advice" and directed me to consult a tax professional. Super frustrating experience.

Thanks for mentioning this! I did have marketplace insurance in 2022 I think. Where exactly do I find those forms if I can't log into my old account?

If you can't access your marketplace account, you can call the marketplace directly at 1-800-318-2596 and request that they resend your 1095-A forms for the years you need. Make sure to have your personal information ready (SSN, DOB, address from that time). Alternatively, you might be able to get the information from the IRS by requesting a tax transcript, though sometimes these forms don't show up completely on the transcript. The best route is definitely going directly through the marketplace if possible.

How do you find someone who specializes in unfiled returns? Just search for "tax resolution" or is there some specific credential I should look for?

But Florida has higher property taxes and insurance costs, right? Did that eat up some of the tax savings?

Can new residents immediately contribute to 401ks? I thought there might be waiting periods or residency requirements for tax-advantaged accounts.

There are no residency requirements for 401k eligibility from a tax perspective - it's based on your employment status, not your citizenship or residency history. As soon as you're legally authorized to work in the US (with appropriate visa/work permit) and your employer offers a 401k plan, you can contribute. Some employer plans do have waiting periods before you're eligible (commonly 3-6 months), but that's a company policy issue, not a tax or legal requirement. Your employer may also have a vesting schedule for their matching contributions, but your personal contributions are always 100% vested. The key thing is having a Social Security Number or Tax ID Number, which you'll need anyway for employment.

1 I actually don't have an accountant yet - part of why I'm in this mess! Been trying to handle everything myself to save money in the first year, but clearly that's not working out so well. Do accountants typically take on new clients same-day when there's a deadline?

3 Many accountants do offer same-day extension filing for new clients, especially during tax season. It's a common way they begin relationships with new business clients who are in a bind. A simple extension filing is low-risk for them and gives you both a chance to work together. I'd recommend calling a few local business accountants and explaining your situation. Be clear that you need the Form 7004 filed today and ask if they can help. Even if they can't take you on as a full client right away, many will handle just the extension filing to help you meet the deadline.

1 Oh crap, I didn't realize that! I haven't calculated what I might owe yet. Is there a quick way to estimate this, or do I need to basically do all the tax calculations anyway?

14 You don't need to do the complete calculations, but you should make a reasonable estimate based on your business income and expenses for the year. A safe approach is to look at what you paid last year (if you were in business) and pay at least that amount. If this is your first year, calculate your rough profit and multiply by the appropriate tax rate. If you're really unsure, it's generally better to overpay slightly and get a refund later than to underpay and face penalties. Even a good faith estimate shows the IRS you're trying to comply, which can help if you end up slightly short.

This is really helpful. I think I might not qualify since the kids are primarily with their mom, but I'll double check the requirements. Do you know if there's any documentation I need to keep in case the IRS questions my filing status?

You should definitely keep records showing when your separation began - any legal separation documents, lease agreement for your apartment showing when you moved out, and anything documenting your custody arrangement. Also save records of all household expenses you paid (rent/mortgage, utilities, repairs, food, etc.) to prove you paid more than half the cost of keeping up a home if you try to claim Head of Household. If the kids are primarily with their mom, you probably won't qualify for HOH. But if she's willing, she could release the dependency exemption to you using Form 8332 (though she'd still claim HOH). This form specifically allows the custodial parent to release the child's exemption to the non-custodial parent.

The stimulus payments were years ago though? I don't think there have been any since 2021. Are you saying we can still claim them somehow if we didn't get the right amount back then?