Can you still use tax software like TurboTax for old returns or do you have to do it all by hand?

You can use tax software for older returns, but you might have to pay for it. Most tax software companies offer prior year versions, but they usually charge for them even if they offer free filing for current year returns. TurboTax, H&R Block, and TaxAct all have options for filing returns from previous years. Just be aware that even if you use software, you'll probably need to print and mail the returns for years older than 2023-2024. The IRS typically only accepts e-filing for the current tax year and sometimes the previous year.

This is super helpful! Does it show everything or could there still be income that doesn't show up that I'd need to report?

14 Do you need to keep any documentation for mileage beyond what the app records? Like gas receipts or anything?

3 For mileage deductions, the app records are usually sufficient since they capture date, distance, and purpose of the trip. You should add notes about the business purpose in the app. You don't need gas receipts for the standard mileage deduction since the IRS rate already accounts for gas, maintenance, and depreciation. However, if you choose the actual expense method instead of standard mileage (which is less common), you would need to keep all those receipts.

1 I'm actually going to be doing marketing and social media consulting. Most of my expenses will probably be software subscriptions, office supplies, and maybe some client dinners/coffees. I won't have much inventory or materials.

19 For marketing/consulting, I'd second the QuickBooks Self-Employed recommendation someone made earlier. I'm in a similar field and it handles those types of expenses perfectly. Just make sure you're clear on what client meals you can deduct - the rules changed a few years ago. Generally client meals are 50% deductible, but for 2023 many business meals were 100% deductible as part of COVID relief measures. A good app should help flag these distinctions.

Thanks for the suggestion! Does TurboTax handle foreign income well? I have earnings from two different countries plus some US investments, so my situation is a bit complicated.

TurboTax does handle foreign income pretty well in my experience. They have specific sections for foreign earned income exclusion (Form 2555) and foreign tax credits (Form 1116). They'll walk you through determining which is better for your situation. For multiple countries, they can handle that too, though you'll need good records of how much you earned in each place and what taxes you paid to each country. The investment income adds another layer, but their premium version specifically covers investment income scenarios. Just be prepared to pay more for the versions that handle international situations.

I used OLT for my 2021 return and it worked fine, but when I tried to do my 2020 return, they only offered paper filing. This was about 6 months ago though, so maybe things have changed. Their customer service was pretty responsive when I asked about it.

Thanks for the info! Guess I'll check with their customer service directly to see if anything's changed. Really hoping to avoid paper filing if possible.

Does this mean I should be using Schedule D instead of Schedule C for reporting ticket resales? I'm so confused now...

For occasional, non-business ticket reselling, Schedule D (Capital Gains and Losses) is typically appropriate since you're selling a capital asset. You'd report the sale price as proceeds, the original ticket cost as your basis, and the difference as your gain. If you're regularly buying and reselling tickets as a business activity, then Schedule C would be more appropriate. The IRS looks at factors like frequency of sales, intent when purchasing, and whether you're running it like a business to determine which is correct. When in doubt, consult with a tax professional who can look at your specific situation.

This is an interesting approach, but risky. The IRS would likely question why the "gifts" were sold so quickly, which makes the gift argument look like tax avoidance. Plus, the 1099-K will still be issued in OP's name since they handled the transaction. I wouldn't recommend this route without proper documentation from the very beginning.

That makes sense. I was thinking there might be a workaround, but you're right - it would look suspicious if the "gifts" were immediately sold. Probably best to just report all the income and deduct the costs as others have suggested. Better to pay the proper taxes than risk an audit!

We haven't received any official letters from the IRS about this yet. Our accountant just called saying his contact at the IRS mentioned there's some kind of "hold" on our claim during a call about something totally unrelated. Super frustrating to get such vague information! We're filing Form 843 to try to get some interest on the delayed amount, but not sure if that will just complicate things further.

That's pretty typical unfortunately. The IRS is seriously understaffed for handling ERC claims, especially the larger ones that get flagged for review. I wouldn't recommend filing Form 843 while your claim is still pending - that could actually create a duplicate file in their system and potentially cause more delays. What worked for us was having our accountant file Form 911 (Taxpayer Advocate Service request) after the 9-month mark, which at least got us assigned to someone who could provide updates.

This is super important! My accounting firm has seen a huge difference in processing times between clients who received earlier ERC payments versus those filing for the first time in 2022-2023. First-time claims over $200k are getting flagged for manual review almost automatically now.