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!

Whatever you do, don't ignore this filing requirement! I made that mistake with my S-corp that had literally no activity for 8 months and ended up with $2,450 in penalties before I realized what was happening. Even explaining to the IRS that the business never operated didn't get the penalties waived.

Yes, you absolutely need to file Form 1120-S for 2023, even with zero activity during your S-corp period. I learned this the hard way when I had a similar situation with my consulting LLC. The IRS filing requirement is triggered by the S-election itself, not by whether you had income or expenses. Since you were an S-corp from July through November 2023, you're required to file for that tax year. The good news is that filing a "zero return" is much simpler than a regular 1120-S. You'll basically be entering zeros in most fields, but you still need to complete all the required schedules (K, K-1, L, etc.). Don't forget to check the "Final Return" box since you revoked the election, and attach a brief statement explaining the S-corp termination date. My advice: don't procrastinate on this! The March 15th deadline comes fast, and those late filing penalties start at $210 per month per shareholder. Even if you file an extension, you need to get that done by the original due date. Better to spend a few hours on paperwork now than deal with penalty notices later.

Just be careful with this strategy. My brother-in-law tried the "continuous business loss" approach for 4 years straight and got audited. Ended up owing back taxes plus penalties because he couldn't prove legitimate business intent. The IRS specifically looked at his purchases of depreciable assets and determined many weren't necessary for the business. Make sure you can demonstrate you're trying to make a profit. Keep good records, have a business plan, separate business accounts, proper bookkeeping, etc. It's not just about the numbers - it's about showing you're running a real business.

One thing I'd add to this excellent discussion is the importance of understanding the "at-risk" rules in addition to the passive activity limitations mentioned. Even if you materially participate in your business, you can generally only deduct losses up to the amount you have "at risk" in the activity. For most small businesses, this means you can deduct losses up to the amount of cash you've invested plus any amounts you've borrowed for which you're personally liable. But if you're using non-recourse financing (where you're not personally liable for the debt), those amounts don't count toward your at-risk basis. Also, regarding the sustainability question - while the hobby loss rule is important, don't overlook the "excess business loss" limitation under Section 461(l). For 2024, if your total business losses exceed $305,000 (or $610,000 if married filing jointly), the excess gets treated as a net operating loss carryforward rather than offsetting your current year income. This mainly affects high-income earners, but it's something to be aware of when planning your strategy. The key is balancing legitimate business deductions with demonstrable profit motive. Document everything, maintain separate business accounts, and consider consulting with a tax professional who specializes in small business taxation.

OMG I FINALLY GOT THROUGH! After 4 failed attempts and hours of my life I'll never get back, I called at EXACTLY 7:00am Eastern on Tuesday and only waited 18 minutes! The agent was actually super helpful and fixed my issue in like 5 minutes once I got through. Keep trying different times and don't give up!

Be careful about what information you share when you do get through. Last year I reached an agent who asked me for information I wasn't comfortable sharing over the phone. Turned out it was legitimate, but always verify you're actually speaking with the IRS before providing sensitive details. They will never ask for full bank account numbers or passwords.

Make sure you keep copies of EVERYTHING you submit. The IRS loves to say they never got stuff 🙄

I was in a similar situation a few years back - missed 2 years and was stressed about it. The good news is you can absolutely file your 2024 return first if you need to, but definitely prioritize getting those back years filed ASAP. One thing that helped me was setting up a payment plan with the IRS for any penalties/interest owed on the missed years. They're surprisingly reasonable to work with if you're proactive about it. Don't let the anxiety keep you from taking action - you've got this!