Did you report each transaction individually or did you consolidate them? I have hundreds of trades and wondering if I need to list every single one or if I can summarize somehow.

I reported each transaction individually because that's the technically correct way to do it. However, if you have hundreds of trades, there is an alternative. You can attach a separate statement to your return that includes all the required information (date acquired, date sold, proceeds, cost basis, gain/loss) and then enter the totals on Form 8949. On the Form 8949 itself, you would check Box C (not reported on Form 1099-B) and write "See attached statement" in the description column. Just make sure your statement has all the same information that would be required on the form itself, organized in a similar format.

Staking rewards are typically treated as ordinary income at the fair market value when you received them, not as capital gains. You'd report these on Schedule 1 as "Other Income." When you eventually sell the tokens received from staking, that would be a capital gain/loss transaction. Your cost basis would be the value at which you initially reported the income (when received).

Do you think it's worth going to a CPA versus an EA for K-1 stuff? I've heard mixed things and I'm not sure if I need the extra credentials for something like this or if I'm just paying for a fancier title.

Both CPAs and EAs are qualified to handle K-1s, but in my experience, the difference comes down to their business model and specialization rather than credentials. EAs often focus exclusively on tax preparation and may have more experience with unusual tax situations for individuals, while some CPAs split their time between tax work and other accounting services. What matters most is finding someone who regularly deals with K-1s and partnership taxation, regardless of which credential they have. I'd recommend interviewing a few preparers and asking specifically about their experience with K-1s from your type of investment rather than just looking at the credentials after their name.

I used FreeTaxUSA last year for my return with 2 K-1s and it only cost $15 total (federal was free, state was $15). Way cheaper than TurboTax's Premier or Self-Employed versions. It handled everything correctly including some complicated passive activity limitations. The interface isn't as polished as TurboTax but it gets the job done well.

This is a great suggestion. Do you typically just call their main number and ask for accounts payable? I'm dealing with a medium-sized marketing agency if that helps.

For medium-sized agencies, I usually check their website first for direct contact info for their finance team. If that doesn't work, yes, calling the main number and asking for accounts payable or vendor management usually works. Marketing agencies tend to be more flexible than large corporations in my experience. Just be polite but firm that you're happy to provide your tax information but prefer to use the standard IRS form. I usually say something like "for consistency in my record-keeping" rather than making it sound like I don't trust their system.

I work in accounts payable and please don't do this. It creates a huge headache for us and will likely result in your documents being rejected or severely delayed. Most large companies have automated systems that flag modified forms for manual review, which puts your paperwork at the bottom of a very long queue.

I've heard mixed things about Cash App Taxes - doesn't it have limitations on which forms it supports? I need to file some investment forms and I think I read somewhere that they don't support all of them. Have you used it with any complex investing situations?

You're right that it does have some limitations. It works for most common investment forms (1099-B, 1099-DIV, etc.), but doesn't support some of the more obscure forms. I have fairly standard investments and it worked fine for me. They don't support foreign income, multiple state filings, or K-1 forms for partnerships. If you need any of those, it wouldn't work for your situation. Their website has a complete list of supported forms that's worth checking against your specific needs before you invest time in entering all your data.

CalFile is great but they have income limits and other restrictions. Worth checking if you qualify first: https://www.ftb.ca.gov/file/ways-to-file/online/calfile/qualifications.html Not everyone will be eligible unfortunately!

Thanks for bringing this up - I hadn't considered the basis limitations! Any simple way to calculate my basis? I've had the S-corp for about 5 years, started with $5K initial investment, and have been putting in some money each year to cover expenses (around $15K total over the years). Never taken any distributions.

Your basis starts with your initial investment ($5K) and increases by any additional capital contributions ($15K) and any income that was reported to you on K-1s over the years. It decreases by losses and any distributions you took. So if you never took distributions, your basis would be $5K + $15K + any income reported on K-1s from previous years - any losses from previous years. You'll need to look at all your old K-1s to track this properly. If your basis went to zero in a previous year, any excess losses would be suspended and carried forward until you have basis again. This is separate from the NOL rules and often catches people by surprise.

I tried using TurboTax for my S-corp NOL last year and it was a nightmare. It kept asking me questions that didn't make sense for an S-corp, and I don't think it properly tracked my basis. I ended up paying a CPA to fix everything and it cost me way more than if I'd just gone to them in the first place.