Oh wow, I had no idea about the estimated payment requirement. Does that happen automatically, or only if the IRS notices a pattern? And is that $1,000 threshold after applying any withholding I might have, or just based on total tax liability?

The estimated tax requirement is based on your final tax return results - it's not subjective or based on IRS discretion. If you owe more than $1,000 after accounting for any withholding you did have, you're generally required to make estimated payments the following year. The requirement is calculated on your total tax liability minus your withholdings and credits. So if your total tax liability is $10,000 and your withholding was only $8,900, you'd owe $1,100 at filing time - triggering the requirement for quarterly payments the following year. This is a statutory requirement, not a penalty the IRS chooses to impose. It's designed specifically to prevent the kind of strategy you're considering.

I've actually had success with balance transfers combined with a proper withholding adjustment (not going exempt, just adjusting to the correct amount). I got a 15-month 0% offer, transferred my high-interest debt, then adjusted my W-4 to account for legitimate deductions I was eligible for. The extra money in my paychecks went straight to paying down the transferred balance before the 0% period ended.

Thanks for breaking that down! Have you ever caught it missing deductions you should have gotten? That's my biggest worry tbh

I have actually caught it missing things a few times over the years. It's generally good at finding common deductions, but it misses some of the more obscure ones unless you know to look for them. For example, last year I realized it didn't prompt me about the student loan interest deduction until I specifically searched for it, even though I had entered student loan information. It's not perfect, which is why it helps to have at least a basic understanding of what deductions you might qualify for.

I've used both. For small business stuff like an Etsy shop, I actually preferred H&R Block. Their self-employment version seemed to ask more relevant questions about business expenses and gave better guidance on what qualifies. TurboTax was more confusing for the business portion in my experience.

Honestly they're pretty similar but I found TurboTax had a slightly better interface. For Etsy specifically though, make sure whichever one you choose can import your Etsy 1099-K directly. Saves a ton of time vs. entering everything manually.

I get what you're saying about the interest-free loan thing, but honestly, for me it's psychological. If I get that money in small amounts in my regular paychecks, I'll just spend it. Having a forced "savings" that comes back as a lump sum helps me actually save for bigger purchases or goals. Plus, I sleep better knowing I won't owe a surprise tax bill!

That's a totally fair point! Personal finance is personal for a reason - if the "forced savings" approach works better for your habits and gives you peace of mind, then it's worth the small amount of interest you might miss out on. If you do decide to go that route, you might want to put a specific dollar amount in Box 4(c) of your W-4 rather than adjusting the other settings. That way you're deliberately setting aside a fixed amount rather than trying to guess at the other settings.

Would the earned income credit apply to someone who was on unemployment for part of the year? I'm trying to figure out if my sister might qualify.

Thanks for the advice! I never thought to manually check what TurboTax was importing - I just assumed the connection to Robinhood would pull everything correctly. Do you think I should just use a tax professional for crypto stuff going forward? Seems like the software isn't reliable enough.

For simple crypto investing, TurboTax or other tax software can still work fine, but you definitely need to manually review what's imported. I actually switched to using a crypto-specific tax preparation tool first (like CoinTracker or Koinly) that generates the proper 8949 forms, then I import those results into TurboTax. If you're doing more complex crypto activities like DeFi, staking, or mining, then yes, a tax professional with crypto experience is probably worth the money. The tax rules are still evolving in this area, and it's easy to make mistakes with the automated tools.

Actually, crypto isn't subject to wash sale rules currently! That's one advantage of crypto - you can sell at a loss and rebuy immediately to harvest the tax loss. This is a big difference from stocks where you have to wait 30 days. But there's talk about changing this soon, so enjoy it while it lasts...

18 How do they even manage all those tax filings? Do they just have a team of accountants? And what happens if they make a mistake on one of them? Seems like a nightmare.

2 Most top tennis players have specialized accountants who focus exclusively on international athlete taxation. These firms typically have partners in each major country where tournaments are held, allowing them to file all necessary returns correctly. If they make a mistake, it's typically handled like any other tax error - they may need to file an amended return and potentially pay penalties or interest if it results in underpayment. The bigger challenge is actually keeping track of exactly how many days they spend in each country, as this can affect their tax residency status and reporting obligations.

10 Yes! Athletes can definitely deduct legitimate business expenses against their tournament earnings. Travel, coaching, training, equipment, medical/physiotherapy, agent fees, etc. are all deductible if they're ordinary and necessary for their profession.