Is there a similar substitute form for missing investment statements? My brokerage is being super slow sending corrected 1099-B forms and that's my main holdup.

Yes, there is! For investment statements, you can use Form 8606 for IRA contributions or Form 8949 for capital gains/losses if you have your own records of transactions. Many brokerages also provide year-to-date transaction history online that you can download even if the official 1099 hasn't arrived. You should document your attempts to get the official forms from your brokerage, including dates you contacted them. For future reference, most brokerages now offer electronic delivery of tax forms which is usually much faster than waiting for mail. I switched to electronic delivery for everything after having similar issues a few years ago.

That matches my experience too. My accountant filed for penalty abatement for me last year when I missed the deadline due to a health emergency. The IRS approved it with minimal questions. They have a "first-time abatement" policy that's pretty generous if you've been compliant in the past.

This! I'm in Virginia and we get a $4,000 deduction per account on our state taxes. Definitely check your specific state rules - some states like Indiana even offer tax credits instead of deductions which are even better.

Exactly right! State benefits vary hugely - Pennsylvania and Montana have unlimited deductions for contributions, while states like Colorado, New Mexico, and others offer deductions up to the annual gift tax exclusion amount. Some states require you to contribute to their specific 529 plan to get the benefit, while others (like Arizona and Kansas) give you the deduction regardless of which state's plan you use. I'd recommend calling your state tax department directly to confirm what's available. The tax savings might not be as big as federal deductions, but they definitely add up over time, especially if you're contributing for multiple children.

8 MONTHS?? Ugh that's so much worse than I thought. Do you know if there's any way to check the status of an amended return after you submit it?

You can check the status of your amended return using the "Where's My Amended Return" tool on the IRS website. You'll need your SSN, date of birth, and zip code. The tool will tell you if it's been received, adjusted, or completed. But honestly don't expect updates very often - mine sat on "received" for about 6 months before changing to "adjusted". The key thing is to pay whatever additional tax you calculate when you submit the amendment. That way even if it takes forever to process, you won't be racking up additional penalties and interest.

This is good advice. I set up a payment plan too after I had to amend 3 years of returns. The interest rates aren't great but way better than credit card debt. And it keeps you from getting nasty letters from the IRS.

That calendar visual idea is brilliant! Did you just use like a regular wall calendar and highlight days, or did you make something digital? I'm not very tech-savvy but could probably figure out a basic spreadsheet if that would look more professional.

I actually did both! I created a digital calendar in Excel where I color-coded days (green for days with me, yellow for days with their mom), and then printed it out. I also made a simple count at the bottom showing the total days for each month and the running total for the year. The judge really appreciated having that visual. Even a hand-colored paper calendar would work fine - the key is making it easy for the judge to see at a glance that you met the six-month requirement. Just make sure you can back up each colored day with some form of evidence. I organized my evidence by month in a binder, so when the judge questioned a particular period, I could immediately turn to that section and show the supporting documentation.

This is all good advice but keep in mind the IRS isn't just looking for evidence you SUPPORTED the kids financially - they specifically need proof the kids LIVED with you for more than half the year. I've seen people bring tons of payment receipts but still lose because they couldn't prove physical residency.

This is a great point about needing a team. Do you recommend finding professionals who already work together or assembling my own team? I'm worried about coordination issues if everyone is working separately.

I strongly recommend finding professionals who already have established working relationships. Ask the CPA you're considering who they regularly collaborate with for estate planning and financial advice. Existing teams will have systems for sharing information efficiently and won't duplicate efforts. The worst scenario is having different advisors giving contradictory guidance. For example, I've seen situations where an investment advisor recommends selling assets that would trigger massive tax consequences the CPA would have advised against. When your team already works together, these issues get addressed before they become problems.

Check out the National Association of Real Estate Tax Professionals (NARETP). I found my CPA through them and it made a huge difference. Multi-state properties create special issues with depreciation tracking and state-specific rules that general CPAs often miss.