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.

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.

Is that actually allowed by the IRS though? Wouldn't they want the payment to come from the person who owes the tax?

The IRS doesn't actually care who makes the payment as long as it's properly credited to your tax account. You just need to make sure the payment includes your name, tax ID number, form type (1040-NR), and tax year. This is common for married couples where one spouse pays both tax bills, parents paying for their kids, or employers paying for employees in some cases. The key is making sure the payment information correctly identifies whose tax account should be credited.

This is terrible advice. The IRS absolutely tracks everything, even small amounts. My friend ignored a $12 balance and two years later got a notice with penalties and interest that had grown to over $40. Just pay what you owe.

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 the enrolled agent help negotiate a lower amount overall or just handle the payment plan? Wondering if it's actually possible to get the IRS to accept less than what they say you owe.

The EA didn't get the actual tax amount reduced - that's rarely possible unless there are actual errors in how your tax was calculated. What they did get reduced were the penalties, which in my case had added about $7k to my original tax bill. They managed to get about $5k of those penalties removed through the first-time penalty abatement program and reasonable cause arguments. They also made sure I was claiming all legitimate business deductions that I had missed on my original filings, which lowered the taxable income and therefore the tax due. This is different than "negotiating" with the IRS - it's just proper tax preparation that I had failed to do correctly.

I tried for an OIC but got rejected. They look at your income, expenses, assets... basically if they think you CAN pay (even over time), they won't accept less. Those radio ads are super misleading. Like 40% of OICs get accepted, and usually for people with serious hardships or very little income/assets compared to their debt.

Thanks for sharing your experience. That's pretty much what I suspected - those ads do sound way too good to be true. I guess I'll look more into payment plans instead since I do have a steady income. Did you end up with an installment agreement after your OIC was rejected?