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.

Does the free version still try to upsell you every five minutes like TurboTax does? I started using their "free" version last year and ended up paying $89 because of some "required upgrade" halfway through.

The IRS Free File options are genuinely free if you meet the income requirements. They're different from going directly to TurboTax or H&R Block's websites, where they often use the word "free" but then upsell you. You need to start through the IRS Free File portal (search "IRS Free File") rather than going directly to the tax software sites. This ensures you get the truly free version that's part of their agreement with the IRS. I've completed my 1040 filing three years in a row without paying a penny using this method.

The EITC income limit for single filers with no qualifying children is way lower than $32k though - I think it's around $17k. So they probably wouldn't qualify unless they have kids?

I got through last Thursday but only after calling literally 12 times. Each time it hung up on me but on the 13th try I got in the queue. Then waited 1 hour 47 minutes to speak to someone. The trick seems to be to keep calling back repeatedly and eventually you'll get lucky and get in the queue instead of getting the "we're too busy" message.

Thanks for the tip! I'll try the persistence approach tomorrow morning. 12 attempts sounds painful but I guess it's worth it if it eventually works. Did you select any specific options in the phone menu that seemed to help get you through?

That's interesting - I did start my taxes in TurboTax but then switched to FreeTaxUSA because it was cheaper. I didn't complete or submit anything in TurboTax though, just started inputting some basic info. Could TurboTax have somehow submitted something without me finalizing it??

It's unlikely TurboTax would submit without you finalizing, but not impossible if there was a glitch. Check your TurboTax account to see if there's any record of a submission. Also, if you used the same email for both tax services, check your email carefully for any confirmation messages that might indicate something was filed. Another possibility: if you had a tax preparer do your taxes last year, sometimes they automatically file extensions for all their clients as a courtesy. Maybe someone filed an extension for you without informing you? Worth checking if that could have happened.