Not OP but I used FreeTaxUSA for crypto last year. It doesn't connect directly to exchanges like some premium services, but you can either enter transactions manually or import a CSV file if your exchange allows exports in that format. If you have tons of transactions, you might want to use a crypto tax service like CoinTracker or Koinly first to generate the required tax forms, then enter the summary into FreeTaxUSA.

Do they save your info from year to year? That's the only thing keeping me with TurboTax right now - I don't want to re-enter everything from scratch next year.

Yes, they definitely save your information year to year! You can import your previous year's return which pulls in all your personal info, employment info, etc. They even keep track of things like depreciation schedules and capital loss carryovers. The transition is pretty seamless if you're switching from another service too - just have a PDF of last year's return handy and you can pull most of the important info from there.

This is such a good point! I tried selling everything when I moved and it was SO time consuming. Some guy literally tried to talk me down from $200 to $40 for my filing cabinet when we met up. I ended up donating half my stuff just to be done with it. Is there a minimum value for tracking donations though? Like do I need to track if I donate a $20 trash can?

For very low-value items like a $20 trash can, you should still track it if you're planning to claim it as part of your total donation, but realistically the IRS isn't going to flag you over small amounts. The general rule is you need receipts for any donation of goods worth $250 or more, and if your total non-cash donations exceed $500 for the year, you'll need to file Form 8283 with your tax return. Once you get over $5,000 in donations, that's when you might need qualified appraisals. During a move, these small items can add up quickly, so keeping a simple spreadsheet with estimated values is a good idea.

Great question! A deduction reduces your taxable income, not your tax bill directly like a credit would. The actual tax savings depends on your marginal tax bracket. For example, if you're in the 22% federal tax bracket and donate furniture with a fair market value of $1,000, your federal tax savings would be about $220 (22% of $1,000). If you also pay 5% state income tax, you might save another $50 there. So in this example, donating $1,000 worth of furniture might save you around $270 in actual taxes. That's why selling can sometimes be more profitable if you can get more than 25-30% of the original value.

Do you know if I have to specify which coins I'm selling for the tax loss? Like if I have 3 different cryptocurrencies all at a loss, can I pick which ones to realize losses on and keep holding the others?

Yes, you can absolutely specify which coins you're selling for tax loss harvesting. You're not required to sell all your underwater positions - you can strategically choose which specific coins and even which specific lots if you've bought the same coin at different times. If you have three different cryptocurrencies at a loss, you can choose to sell just one or two and keep holding the other. You might base this decision on which coins you're least confident about long-term or which would give you the biggest tax benefit. Some tax software lets you optimize this by showing which sales would be most beneficial.

Yep, same forms as stock trades. Form 8949 is where you'll list all your crypto transactions, and then the totals carry over to Schedule D. Make sure you check the correct box at the top of Form 8949 depending on whether the transactions were reported on a 1099-B. For most crypto exchanges in 2025, you'll likely check box C since many still don't issue 1099-Bs (though this is changing). Keep all your transaction records because the burden of proof is on you!

That's a really good point about deductions. Do I need to file a Schedule C for the contractor income? And is it worth looking into setting up an LLC or something like that for tax purposes?

Yes, you'll need to file Schedule C to report your business income and expenses as a self-employed person. This is where you'll list all those deductions I mentioned. Regarding an LLC, it probably isn't necessary just yet at your income level. An LLC by itself doesn't change how you're taxed - you'd still file Schedule C. It mainly provides liability protection, which may not be crucial depending on what type of contract work you're doing. If your business grows substantially or has liability risks, then consider it. But for now, focus on tracking expenses and making your quarterly estimated tax payments.

An S-Corp can save on SE taxes, but only makes sense once you're making at least $60-80k from your independent work. At $27k, the extra costs of running an S-Corp (separate payroll, more complex tax filing, annual fees) would likely outweigh any tax savings. Plus you'd need to pay yourself a "reasonable salary" which would still be subject to FICA taxes. The tax savings only apply to distributions above that reasonable salary amount. For smaller amounts of contract income, stick with Schedule C filing.

Thanks for sharing your experience! Do you think it matters that my contract with the Malaysian company says "employment agreement" in the title, even though the substance of the relationship is more like self-employment? Did you have a similar issue with your German contract?

The title of the contract isn't as important as the actual terms within it. My German agreement also said "employment contract" but the IRS looks at the substance of the arrangement more than the labels. Make sure you highlight aspects of your arrangement that support self-employment: you paying your own expenses, setting your own schedule when possible, using your own equipment, and the lack of typical employee benefits. In my case, I included a memo with my tax return briefly explaining why I was filing as self-employed despite the contract title, focusing on these substantive factors. The key is being consistent and having documentation to back up your position if questioned.

I used TurboTax last year for a similar situation working in Thailand. It does handle Schedule C for self-employment and Form 1116 for Foreign Tax Credit, but honestly the questionnaire was confusing for international situations. I ended up having to manually override some things and do quite a bit of research on my own. If your situation is straightforward self-employment, it might work fine, but if there are complexities, you might want a professional who specializes in expat taxes.

Thanks for the insight! I might try TurboTax first since my situation isn't super complex, but keep a tax professional as backup if I get stuck. Did you find any specific resources that helped you figure out the overrides you needed to make?