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.

That's incredibly frustrating to learn! I had no idea there was actually a proposed system that got killed by industry lobbying. I just looked up that ProPublica article and wow... the fact that other countries have been doing this for decades while we're stuck manually entering numbers that the government already has is ridiculous. Do you know if there's any movement to revive this idea? Seems like the kind of common sense thing that both political parties could potentially get behind.

There have been several attempts over the years, most recently the Tax Filing Simplification Act that's been introduced a few times but hasn't passed. The current administration has made some promises about simplifying the tax filing process, but meaningful change faces the same powerful lobbying obstacles. The Free File agreement was actually modified in 2019 after the ProPublica reporting, removing the provision that explicitly prevented the IRS from creating its own system. That's a start, but there's still strong resistance. The best hope is continued public pressure and awareness - the more people understand that better options exist and are being deliberately blocked, the more momentum builds for change.

This makes me want to move to Australia just for the tax system lol. Do they at least buy you dinner before they take your money? The US system is just insult to injury - "figure out how much you owe us or go to jail, but also we won't make it easy, and ps we already know the answer.

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.

Did you use specific tax software that handled this well? I'm worried about messing up the reporting when I eventually sell.

I actually used TurboTax Premier, which has a specific section for stock sales and options. It prompts you to enter all the information from your Form 3921 and walks through calculating your basis properly. H&R Block's premium version also handles this well, but I found TurboTax's interface more intuitive for entering multiple stock option transactions. Just make sure you have all your documentation ready before you start, as you'll need to enter details like exercise dates, fair market values, and exercise prices for each transaction.

That happened to my brother! The company IPO'd at like 5x the last private valuation and suddenly everyone was scrambling to figure out their tax situations. Did you end up owing a bunch in taxes that year?

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.