Watch out with TaxAct - they've been gradually increasing prices the past few years. My first year was super cheap, but by year 3 they had nearly doubled in price. Still cheaper than TurboTax but the gap is closing. The tax software companies all seem to do this "introductory pricing" thing.

Great breakdown! I've been procrastinating on my taxes partly because of TurboTax's ridiculous pricing increases. Your side-by-side comparison is exactly what I needed to see. Quick question - did you notice any difference in the audit protection or customer support between the two? TurboTax always pushes their "audit defense" add-on but I'm wondering if that's just another way to extract more money from customers. Also, for anyone else considering the switch - make sure to download/save a copy of your previous year's return before you lose access to your old tax software account. Learned that the hard way when I switched between services a few years back and needed my prior year info for comparison. The $100+ savings you found would easily cover a nice dinner out to celebrate getting your taxes done! 🎉

Thanks for sharing all this detailed QSBS information! As someone new to this community, I'm finding this thread incredibly helpful. I'm in a similar situation with a startup I joined 4 years ago that's now looking at potential exits. One question I haven't seen addressed yet - does the company need to formally certify that it qualifies as QSBS, or is this something we determine ourselves when filing? Our company lawyer mentioned something about getting a QSBS election or certification, but I'm not sure if that's required or just recommended for documentation purposes. Also, for those who have successfully claimed the exclusion - did you face any additional IRS scrutiny or audits? I'm wondering if claiming such a large exclusion automatically triggers more review from the IRS.

Great thread on QSBS! I'm new to this community but have been following startup tax issues closely. One aspect I haven't seen mentioned yet is the importance of tracking the "active business" requirement throughout your entire holding period - not just at the time of stock issuance. The 80% active business test under Section 1202(e) needs to be met during substantially all of your holding period. I've seen cases where companies started as qualifying businesses but later failed this test due to passive investments or real estate holdings growing too large relative to their active operations. For anyone holding QSBS long-term, it's worth requesting annual confirmations from your company's finance team that they're still meeting this requirement. The last thing you want is to discover at sale time that your stock lost QSBS status in year 3 due to the company's investment strategy. Also, keep in mind that if you're planning a sale in the near future, you may want to consider the timing relative to potential tax law changes. While QSBS has been relatively stable, it's always been subject to political discussions about reform.

Just a personal experience - I didn't file my 2021 taxes until last March (so over a year late) and I ended up owing about $1800 in taxes plus around $400 in penalties and interest. The longer you wait, the worse it gets. File ASAP even if you have to use incomplete information and then amend later. A rough filing now is better than a perfect filing months from now when it comes to penalties.

I was in almost the exact same situation last year - missed filing 2022 taxes due to a job change and cross-country move. The stress was eating me alive until I finally bit the bullet and filed. Here's what I learned: if you're getting a refund (which many people are), there's literally NO penalty for filing late. The IRS isn't going to penalize you for being late to collect money they owe you. You just lose the refund if you wait more than 3 years. If you do owe money, the failure-to-file penalty is brutal (5% per month), but here's the key - it stops accumulating once you file. So even if you can't pay immediately, filing stops the bleeding on the biggest penalty. My advice: gather whatever documents you have and file this weekend. Don't wait for every single paper to be perfect. You can always amend later if needed, but getting that return filed stops penalties from growing and gives you options for payment plans. The relief I felt after finally submitting was incredible - way better than the months of anxiety I put myself through by procrastinating.

This might be a dumb question but does anyone know a good tax software that handles options trading well? I've been using H&R Block but it seems totally confused by my covered calls and cash-secured puts.

I've been dealing with the same TD Ameritrade 1099-B confusion for years! One thing that really helped me was understanding that the "basis reported to IRS" distinction basically tells you how much work you have to do. When TD reports the basis, they're telling the IRS what you paid - so you just need to make sure your tax software captures the right gain/loss. When they don't report basis, you're on the hook to prove what you paid if the IRS ever asks questions. For your $63k trading volume, definitely pay attention to the wash sale adjustments. TD Ameritrade is pretty good about calculating these, but they only track wash sales within their own system. If you have accounts at other brokers or bought the same securities in a retirement account, you'll need to manually track those wash sales yourself. Also, since you mentioned futures trading - those Section 1256 contracts are actually treated more favorably tax-wise because of that 60/40 long-term/short-term split, regardless of holding period. So even if you held a futures contract for just one day, 60% of the gain gets long-term capital gains treatment. Pretty nice tax advantage compared to regular stock trading!

Great question about S-Corp basis tracking! As someone who went through this same confusion a few years ago, I can share what I learned from my CPA. For your specific questions: 1. Yes, use the K-1 Part III, but don't just focus on Box 1. You need to look at ALL the boxes - income items (Boxes 1-10) generally increase basis, while deductions and losses (Boxes 11-13) decrease it. Also check Box 16 carefully for distributions and other adjustments. 2. Unfortunately no - there's no single summary box. The IRS expects shareholders to maintain their own basis calculations, which is honestly one of the more frustrating aspects of S-Corp ownership. 3. Since there's no official place this appears on returns, you'll need to reconstruct from Day 1. Start with your initial investment/contribution when you formed the S-Corp, then work through each year's K-1 systematically. One critical tip: Make sure you're handling the ORDER of adjustments correctly. Income and contributions increase basis first, then losses and deductions reduce it, and finally distributions come out last. This order matters because it affects how much loss you can deduct in any given year. Given your simple structure (sole owner, no loans, minimal complexity), your calculation should be straightforward once you get the methodology down. I'd strongly recommend setting up a tracking system now so you don't have to reconstruct again in the future!

I've been through this exact same struggle with my S-Corp basis tracking! One thing that really helped me was creating a running basis worksheet that I update quarterly instead of waiting until year-end. A few practical tips from my experience: 1. Don't forget about estimated tax payments - these don't directly affect your S-Corp basis, but they're important for cash flow planning alongside your basis calculations. 2. If you've made any equipment purchases through the S-Corp that you elected to expense under Section 179, make sure you're accounting for those properly in your basis calculation. The deduction flows through to your personal return but can affect basis. 3. Keep detailed records of ANY money you put into or take out of the business bank account. Even if something seems minor, it might be relevant for basis purposes. Since you mentioned you've always taken distributions less than your estimated basis, you're probably in good shape, but getting the exact numbers will give you peace of mind and help with future planning. The reconstruction is tedious but absolutely worth doing correctly!