Thanks for the response! I probably have about 15-20 transactions total. Not a ton, but enough to be annoying to calculate manually. There were definitely price movements between when I bought the BTC and when I traded it... some trades I made when BTC was way up and others when it had dropped.

With 15-20 transactions and significant price movements, it's probably worth using either TaxAct's crypto feature or one of the specialized services others have mentioned. Trying to manually calculate 20 transactions with varying cost basis is error-prone and time-consuming. Make sure you also track the cost basis of those other coins you received in the trades, because when/if you eventually sell or trade those, you'll need to know what they were "worth" when you acquired them to calculate future gains/losses. This is where specialized crypto tax software really helps, as it maintains that chain of cost basis calculations.

Yes, you should still report it. The silver lining is that those losses can offset other capital gains or up to $3,000 of ordinary income. So reporting your crypto losses could actually reduce your overall tax bill!

That makes so much more sense! I think that's exactly what my friend was talking about - getting help from a retirement planner, not some tax form I was missing. This has been stressing me out for days! So just to confirm, for a normal contractor with 1099 income, I just need to file Schedule C with my regular tax return, right?

Exactly! As a contractor receiving 1099s, Schedule C is your main form for reporting business income and expenses. You'll also need Schedule SE for self-employment tax. Those are the standard forms for independent contractors. If you have a retirement account like a SEP IRA or Solo 401(k), you might have additional forms, but there's no specific "CRP" form involved in standard contractor tax filing.

I used FreeTaxUSA last year for my Schedule C filing and it worked great. It's not part of the IRS Free File program, but it's only $15 for state filing and federal is free. Way cheaper than TurboTax and handled all my contractor income perfectly.

That's actually a really good idea! I hadn't thought of trying a third one as a tiebreaker. I'll give TaxSlayer a shot tonight and see if it aligns with either Keeper or FreeTaxUSA. I'm guessing if two of them match, that's probably the right calculation? Though with my luck all three will show different amounts lol.

Yeah, exactly - if two match and one is different, that's usually a good indication. And with three states and multiple 1099s, it's worth the extra effort to be sure. Just make sure you're entering everything identically in all three systems. I found sometimes even the order of entering certain forms can affect calculations in weird ways. Let us know which one ends up matching!

In my experience, TurboTax seems to handle the QBI (Qualified Business Income) deduction best for multi-state situations. I had issues with H&R Block last year where it wasn't properly allocating the QBI between states. Maybe try that as your third option?

Thanks for the tip! I didn't want to spend the money on TurboTax since it's so expensive compared to the others, but if it handles QBI better it might be worth it. Definitely seems like that could be part of my issue.

I thought TurboTax and TaxAct only have free versions if your return is super simple? I have investment income and a home office deduction so I always assumed I'd have to pay for the premium versions. Did you have any complex situations on your return?

You're partly right - the completely free versions are limited, but they're more comprehensive than most people realize. I have some dividend income and capital gains, and TaxAct's free version handled those fine. For more complex situations like home office deductions, you might need to use their paid version, but it's still much cheaper than paying an accountant. I found that the Deluxe version was only around $25 when I started with the free version then upgraded only for the features I needed. Completely worth it to avoid the stress of technical glitches like that checkbox issue!

Thanks for this info! One question - do you happen to know if the calculator in the forms is at least smart enough to add this automatically based on birthdate? Or do we need to manually do the math for line 12a?

The calculator doesn't automatically adjust for age or blindness since it relies on those checkboxes working properly. You'll need to manually calculate your standard deduction amount by adding your base standard deduction plus the additional amounts I mentioned. For 2024 taxes, the base standard deduction amounts are $14,600 for single/HOH, $29,200 for married filing jointly. So for example, if you're single and over 65, you'd manually enter $14,600 + $1,850 = $16,450 on line 12a. The system won't do this calculation for you because of the checkbox malfunction.

Do you need to verify those certificates somehow? Or just keep them on file? I've had a few business customers claim they're exempt but I wasn't sure if I should just take their word for it.

You need to collect the actual certificate from them - don't just take their word for it. Most states have specific forms customers need to fill out. You should verify the certificate has all required information (their tax ID number, signature, etc.) and keep it on file. Some states also let you verify tax ID numbers on their websites. You don't need to send these certificates to the state, but you absolutely must have them available if you get audited. I now keep digital copies of all certificates in a dedicated folder so I can find them easily.

I've used both. TaxJar is more affordable for small businesses but Avalara has more features if you're growing fast. With your sales level ($2,500/month), TaxJar's basic plan would probably be sufficient. The time savings is definitely worth it - it automatically files your returns in multiple states and keeps track of all the weird local tax rates.