Thanks for this advice. My income has actually decreased quite a bit since 2022 (lost my higher paying job). Would that potentially help me qualify for an Offer in Compromise? And is that something I can apply for myself or do I need a professional?

Yes, a significant decrease in income could definitely help qualify you for an Offer in Compromise. The IRS looks at your current income, expenses, asset equity, and future earning potential to determine if you can reasonably pay the full amount owed. You can absolutely apply yourself using Form 656, though it's a complex process requiring detailed financial documentation. There's a $205 application fee, but it's waived if you meet low-income certification guidelines. If you decide to go this route, be extremely thorough with your financial information. The IRS rejects most offers that are incomplete or don't accurately reflect your ability to pay. There are good resources on the IRS website to help you through the process if you want to try it yourself.

Did they charge you a lot in penalties? I'm in a similar situation and worried about how much extra I'll end up owing beyond the original taxes.

How did FreeTaxUSA handle the estimated tax payment calculations? That's the part I'm most confused about because my accountant never really explained why I needed to pay them or how they were calculated.

FreeTaxUSA has a really good estimated tax calculator that shows you exactly why you need to make payments. It breaks down how much of your income doesn't have taxes withheld (like your dividends and any crypto gains), and then calculates the quarterly payments you need to make to avoid penalties. The system also explains that you generally need to pay estimates when you expect to owe more than $1,000 at tax time. In your case, the combination of your investment income and crypto probably pushed you over that threshold. The software will generate estimated payment vouchers with the exact amounts and due dates for each quarter, which makes it super straightforward.

But what software do you use? And how do you handle the K1? That's the part that seems most complicated to me.

Didn't they actually try to make a "postcard-sized" tax form a few years back? Whatever happened to that? Seems like my tax return gets thicker every year.

They did try to make that simplified postcard form around 2018 as part of the tax law changes. It was basically a marketing gimmick - they just moved all the calculations to separate worksheets and schedules that you still had to fill out. The whole thing was abandoned pretty quickly because it actually made filing more complicated, not less. Now tax returns are definitely getting thicker every year with more worksheets and schedules than ever. The 2023 tax year is no exception with all the special credits and deductions they keep adding without simplifying the old ones.

Try using tax software. It walks you through all that stuff step by step. TurboTax, H&R Block, or even the free options like FreeTaxUSA handle all those worksheets and calculations behind the scenes.

Thanks for the advice! Just to clarify - are there income limits for Roth 401k contributions? I thought those were just for Roth IRAs.

You're absolutely right, and I should have been clearer. There are no income limits for Roth 401k contributions - those limits only apply to Roth IRAs. With your combined income, you would likely be in the phase-out range for direct Roth IRA contributions, but your Roth 401k contributions are completely fine regardless of income level. That's one advantage of the 401k version.

I wouldn't delay a major life decision like buying a house just for tax reasons. The benefits of homeownership typically outweigh any short-term tax optimization.

Good point. I guess I was just thinking about our experience where the timing of our home purchase affected which year we could first claim certain deductions. But you're right - probably not worth delaying such a major life decision.

9 Do you recommend any specific apps for tracking expenses? I always lose my receipts and then panic at tax time trying to piece everything together from bank statements.

5 I usually recommend QuickBooks Self-Employed for content creators as it lets you categorize transactions easily and tracks mileage automatically if you travel for content. It also helps separate business from personal expenses. For a simpler option, many of my clients use free apps like Everlance or just a dedicated spreadsheet with photos of receipts stored in Google Drive. The key is consistency - pick a system you'll actually use and stick with it all year rather than scrambling at tax time.

14 This isn't entirely accurate. The requirement for quarterly estimated taxes isn't based on a specific income threshold but whether you'll owe $1,000+ at tax time. Even with $3-4K in side income, you could potentially hit that depending on your overall tax situation.