I definitely had well over the threshold. Made about $12k in trades throughout the year with both gains and losses, and received around $500 in dividends. I should definitely be getting forms. Actually just checked my account again after reading all these responses, and my documents finally appeared this morning! Seems like they're rolling them out in batches. Thanks for all the suggestions though - I'll check out that taxr.ai tool next year to avoid the waiting game.

I've used Robinhood for 3 years and haven't had any audit issues. Their 1099-B can be confusing though - they split everything into sections like "Covered", "Noncovered", and "Unknown" securities. Make sure you report everything correctly. Their cost basis reporting has improved a lot but still isn't perfect.

That's a great point I hadn't considered! Do you know which states typically don't conform with the federal rules? I have properties in Arizona and Florida besides my home state.

California is the big one that doesn't fully conform to federal bonus depreciation. Florida fully conforms to federal rules, which is good news for you. Arizona partially conforms but has some modifications - they spread the bonus depreciation over 5 years instead of taking it all upfront like the federal. For your situation with Arizona properties, you might not get the full depreciation benefit on your state return that you'd get on your federal return. This makes proper state tax planning really important when you have multiple properties across different states. I learned this the hard way and ended up with an unexpected state tax bill.

Unfortunately, the sales are already complete as part of the divorce settlement. I had to liquidate certain properties by court order, so a 1031 exchange wasn't possible in my situation. That's why I'm scrambling for other tax strategies now.

Would it be better to mail each year in separate envelopes? I've heard the IRS might lose multiple returns if they're bundled together. Also, should I send them certified mail?

Definitely mail each year in its own separate envelope. I should have been clearer on that point. You want them to arrive around the same time, but not physically bundled together, as each year needs to go through its own processing. And yes, absolutely use certified mail with return receipt requested for every return you send. This gives you proof of when you filed in case anything gets lost in their system. Keep those receipts forever - I'm not exaggerating. The IRS can come back years later asking questions, and having proof you submitted returns is crucial.

The "Fresh Start" program isn't a specific program you apply for - it's a collection of different IRS policies that make it easier to resolve tax debts. It includes things like: 1. Streamlined installment agreements up to $50,000 2. Offer in Compromise changes that make it easier to settle for less than you owe 3. Tax lien changes that make liens less damaging to your credit You don't need to pay someone $3000 to access these - they're standard IRS procedures you can use yourself once you've filed all required returns.

Do you know if Direct Pay works for quarterly estimated tax payments too? I'm self-employed and always forget to mail those vouchers on time.

Yes, Direct Pay works great for quarterly estimated tax payments! That's actually how I use it most often since I'm partially self-employed. You just select "Estimated Payment" as the payment type instead of "Tax Return." It's super convenient because you can schedule all four quarterly payments at once at the beginning of the year (or any time before each due date). The system will send you email reminders before each payment processes, and you can cancel or modify the payment up to two business days before the scheduled date if your situation changes.

Thank you so much for this advice! I actually did take screenshots of my payment confirmation page from TurboTax showing the date I authorized the payment and the account info. I'll make sure to keep those safe. Did the IRS eventually remove the penalties in your case without much trouble once you showed them the proof?

Yes, they did remove all penalties once I provided the documentation, but it wasn't exactly a smooth process. I had to call multiple times and got different answers from different agents. Eventually I had to send a formal written appeal with copies of my screenshots and payment confirmation. About three weeks after submitting that, I received a letter confirming the penalties were removed. The key was having that screenshot showing the exact date and time I authorized the payment. Without that specific evidence, I think they would have kept the penalties in place. So you're already ahead of the game by having those screenshots - just keep them somewhere safe for at least three years!

Do capital losses offset the Net Investment Income Tax as well? I had some gains but also some pretty big losses this year.

Yes, capital losses do offset gains before calculating the Net Investment Income Tax. The NIIT applies to your "net" investment income, so losses are factored in before determining if this additional tax applies. If your losses exceed your gains, you can use up to $3,000 of the excess to offset your ordinary income, and any remaining losses can be carried forward to future tax years. This can be a helpful strategy if you're near the NIIT threshold.

That's a really good point. Does anyone know which states don't tax capital gains? I'm thinking about moving soon and this could be a factor.

That's right! Tax-free states include Florida, Texas, Washington, Nevada, Alaska, Wyoming, South Dakota, New Hampshire, and Tennessee. There are also states with special treatment for capital gains like Arizona and Montana that offer partial exclusions in some cases. But watch out for other taxes these states might have instead - some have higher property taxes or sales taxes to make up for the lack of income tax. Total tax burden is what really matters for your bottom line.