Another option worth considering is FreeTaxUSA's built-in crypto import feature. I switched from TurboTax last year partly because of how much easier they made crypto reporting. You can directly upload CSV files from most major exchanges without needing to convert to TXF first. The software automatically calculates cost basis using FIFO method and handles crypto-to-crypto trades correctly. Plus FreeTaxUSA is significantly cheaper than TurboTax - their Deluxe version that includes investment/crypto reporting is only $14.99 compared to TurboTax's $89+ for similar features. I know switching tax software mid-season isn't ideal, but if you're having ongoing issues with CSV to TXF conversions, it might be worth considering for next year. They also have better customer support response times in my experience, so you're less likely to need services like Claimyr to get through to someone.

For those dealing with really large numbers of transactions (1000+), I've found that breaking the CSV files into smaller chunks before conversion helps avoid timeout errors and memory issues with most conversion tools. I usually split my annual transaction history into quarterly files of 200-300 transactions each, convert each chunk separately to TXF format, then combine them into a single file for TurboTax import. This approach has worked well with both the GitHub Python scripts mentioned earlier and the paid services like taxr.ai. One thing to watch out for - make sure you maintain chronological order when splitting files, especially if you're dealing with crypto-to-crypto trades where cost basis calculations depend on previous transactions. I learned this the hard way when my FIFO calculations got messed up because I sorted transactions alphabetically instead of by date. Also, always keep a backup of your original CSV files before making any modifications. I've had conversion tools occasionally corrupt data or introduce formatting errors that weren't immediately obvious until I tried to reconcile the final numbers.

Did your grandfather's estate go through probate? Just wondering because my uncle left me money but the estate is still in probate and i haven't gotten anything yet. It's been like 8 months!

Just wanted to share my experience since I went through something similar last year. My grandmother left me about $52,000 and I was panicking about taxes too. The good news is that everyone here is right - you don't owe federal income tax on the inheritance itself. However, make sure you keep good records of when you received it and the amount. While you won't need to report it as income, it's good documentation to have. Also, if you decide to invest that money, keep track of your original $47,000 so you know your basis for any future investments. One thing that helped me was setting aside a small portion in a separate savings account just for any potential tax obligations on future earnings from the inheritance. That way I'm not tempted to spend money I might owe taxes on later. California doesn't have inheritance tax like you mentioned, so you're all set there too. Congratulations on the inheritance - I'm sure your grandfather would be happy knowing it's helping you!

Be careful about capital gains tax rates depending on how long you've owned the property! If you've owned it for more than a year, you'll pay the lower long-term capital gains rate (0%, 15%, or 20% depending on your income). If less than a year, you'll pay at your ordinary income tax rate which is likely higher.

One more thing to keep in mind - if the cabin was inherited, you likely get a "stepped-up basis" which means your cost basis is the fair market value when you inherited it, not what your grandparents originally paid. This can significantly reduce your capital gains tax! For example, if your grandparents bought the cabin for $50,000 but it was worth $200,000 when you inherited it, your basis is $200,000. If you sell it for $250,000, you only pay capital gains on the $50,000 difference, not the full $200,000 gain from the original purchase price. Make sure you have documentation of the property's value at the time of inheritance (like an appraisal from the estate) since this will be crucial for calculating your actual taxable gain. This could save you thousands in taxes compared to what you might initially think you owe!

Has anyone used TurboTax for reporting 1099-K for their casual sales? I'm in a similar situation and wondering if it walks you through estimating costs properly or if I need something more specialized.

I went through this exact situation two years ago with my vintage book selling. Here's what I learned from my CPA: The IRS actually has guidance for situations where exact records don't exist. You can use what's called "reasonable reconstruction" of costs. What I did was create categories based on where I typically shop and what I usually pay. For example: "Garage sale paperbacks: $0.25-$1.00 each" or "Estate sale hardcovers: $2-$5 each." Then I applied these ranges to my sales based on what I could remember about each item's source and condition. The key is being conservative and consistent. Don't inflate your costs, but don't shortchange yourself either. Document your methodology - write down how you arrived at your estimates. If you sold 50 books for $20 each that you estimate cost you $3 each on average, show that math. Also start keeping better records NOW. Take photos of items with any visible price tags when you buy them. Keep a simple log in your phone. The IRS is much more forgiving when they see you're making a good faith effort to track things properly going forward. For your $11,475 in sales, estimating $8,000-$9,000 in costs sounds reasonable based on your description. Just make sure you can explain how you arrived at that number if asked.

Don't forget you can also deduct equipment you buy for the team if it's not reimb

Great question! I've been in a similar situation volunteering with youth basketball. One thing that really helped me was keeping a detailed log from day one - not just mileage, but also dates, times, and purposes of each trip. The IRS can be pretty strict about documentation for volunteer deductions. Also worth noting that if you use your personal vehicle for volunteer work, make sure you're not double-dipping by claiming both the charitable mileage rate AND actual gas expenses - it's one or the other. The standard rate often works out better anyway since it covers wear and tear on your vehicle too. Have you checked if your league provides any documentation at year-end? Some organizations will send volunteers a summary letter acknowledging their service and expenses, which can be helpful for your records.