Another option if you're still stuck is to check with your tax preparer or CPA if you used one during the years around when you purchased the stock. Sometimes they keep copies of old tax returns that might have records of dividend income from that stock, which could help establish when you owned it and potentially give clues about your purchase timing. Also, don't forget to check your old bank statements if you still have access to them online. Many banks keep records going back 7+ years, and you might find the withdrawal or transfer that funded the stock purchase. Even if it doesn't give you the exact cost basis, it could help narrow down the purchase date and amount, which you can then cross-reference with historical prices. The key thing is to document whatever method you use and keep records showing you made a good faith effort. The IRS is generally reasonable about these situations when you can show you tried to find the actual information.

I went through something very similar about two years ago with an old Fidelity account. What ended up working for me was a combination approach that might help you too. First, I contacted Schwab's customer service and specifically asked to speak with someone in their "account reconstruction" department - apparently they have specialists who deal with exactly these kinds of missing cost basis issues from acquisitions. The regular customer service reps couldn't help, but this specialized team had access to more historical TD Ameritrade data than what shows up in your online account. When that didn't get me everything I needed, I used the IRS's own guidance from Publication 551. They actually have a section that covers "Unknown or Indeterminable Cost" and provides a framework for making reasonable estimates. The key is being able to show you made a good faith effort to find the actual information. I ended up creating a simple spreadsheet documenting: 1) All the places I looked for records, 2) The approximate timeframe I remembered buying (even if it was just "sometime in 2011-2012"), 3) Historical price data from that period, and 4) My reasoning for the estimate I used. I attached this as a statement with my tax return. The IRS never questioned it, and my CPA said this approach shows due diligence while being conservative about not understating the tax owed. Much better than using zero and overpaying significantly.

Definitely file the 1099-C! I didn't do this with a former tenant and regretted it. I forgave about $3,000 in back rent, didn't file the form, and then couldn't claim the loss properly on my taxes. My accountant said without the 1099-C documentation, the deduction looked questionable.

Just wanted to add my experience as someone who's dealt with this multiple times. You absolutely should file the 1099-C - it protects you and creates a clear paper trail for the IRS. I've had three situations where tenants left owing significant rent, and filing the 1099-C each time made my tax filings much cleaner. A few practical tips: Make sure you have the tenant's correct SSN from their original rental application before filing. If you don't have it, you'll need to make a reasonable effort to obtain it. Also, keep copies of all your documentation - the lease, payment records, eviction notices, etc. The IRS may want to see proof that the debt was legitimate and that you actually made the decision to cancel it. One thing that caught me off guard the first time - you need to send a copy of the 1099-C to the tenant as well as the IRS. Don't just file it and forget about it. The tenant needs to receive their copy by January 31st too.

For those items where you absolutely can't establish a cost basis through any reasonable method, keep in mind that the IRS could potentially consider your basis to be $0, meaning you'd pay capital gains tax on the entire proceeds. That's the worst-case scenario you want to avoid. This happened to a friend with a coin collection - couldn't establish basis for about 20% of it, and ended up paying tax on the full amount for those pieces. Pretty painful tax hit!

This is such a valuable discussion! I've been putting off dealing with my stamp collection for years because I was worried about this exact issue. One thing I'd add - if you're in a similar situation, start documenting everything NOW before you sell. Take photos of your items with current dates, write down everything you remember about when and where you bought them, and gather any supporting evidence you can find (old bank statements, insurance records, etc.). I learned the hard way that trying to reconstruct this information after you've already sold items is much harder than doing it beforehand. The IRS appreciates seeing that you made a systematic effort to establish your basis rather than just scrambling at tax time. Also, for anyone dealing with inherited collectibles - the rules are different! You might get a "stepped-up basis" equal to the fair market value when you inherited them, which could save you a lot in taxes. Definitely worth looking into if that applies to your situation.

I switched from joint to separate filing two years ago and learned some hard lessons. Here are the key things that caught me off guard: **Immediate Tax Impact:** - Lost about $2,800 in combined refunds compared to joint filing - Standard deduction dropped from $25,900 to $12,950 each - Lost eligibility for several credits we'd been claiming **Ongoing Complications:** - Had to split itemized deductions carefully (mortgage interest, property taxes, etc.) - One spouse itemizing meant we BOTH had to itemize even when standard would've been better - State taxes became more complex since our state doesn't allow separate filing **Unexpected Restrictions:** - IRA contribution limits became much stricter - Some retirement plan contributions were no longer deductible - Capital loss deduction was capped at $1,500 instead of $3,000 The process itself was more work too - essentially preparing two returns and coordinating between them. We did it for student loan payment reasons and it worked out financially overall, but barely. I'd strongly recommend using tax software to model both scenarios with your actual numbers before deciding. The "what if" calculators can show you exactly what you'll gain or lose.

I went through this exact situation two years ago! Here's what I wish someone had told me upfront: **The Good News:** - You can still change your mind before filing - prepare both ways to compare - If you're doing this for student loan payments, the monthly savings might offset higher taxes - You do get protection from spouse's tax issues/liabilities **The Reality Check:** - We paid about $2,100 more in combined taxes filing separately - Lost eligibility for American Opportunity Credit (was getting $2,500/year) - Roth IRA contribution limits dropped dramatically due to separate filing income thresholds - Had to coordinate who claims dependents and how to split deductions **My Process:** 1. Used TurboTax to prepare our return both ways before deciding 2. Calculated the actual dollar difference in taxes owed 3. Compared that to the monthly savings on student loan payments 4. Factored in lost credits and deduction limitations For us, the student loan payment reduction ($380/month) made it worthwhile despite the tax hit. But it was close! I'd strongly recommend running the numbers both ways with your actual income/deductions before deciding. The tax software comparison tools are really helpful for seeing the full picture. And remember - you can switch back to joint filing next year if separate doesn't work out. What's your main reason for considering the switch? That might help others give more targeted advice.

I'm a bookkeeper and I see this ALL THE TIME with new S-Corps. Here's a step-by-step approach: 1. Open separate accounts today 2. Print all bank/credit statements since S-Corp formation 3. Create a spreadsheet tracking every transaction 4. Mark each as business or personal 5. Calculate total personal expenses paid from business account 6. Calculate total business expenses paid from personal accounts 7. Do a reconciling transfer to make the accounts whole 8. Set up proper payroll immediately 9. Document EVERYTHING with a memo explaining the situation The worst thing you can do is ignore it. I've helped clients navigate IRS inquiries on this exact issue, and they're much more lenient when you've identified and fixed the problem yourself.

I went through almost the exact same situation with my S-Corp about 18 months ago. The panic when you realize what a mess you've created is real, but it's absolutely fixable! Here's what worked for me: I immediately opened separate business accounts and stopped all commingling that day. Then I hired a CPA who specializes in S-Corps (not just any accountant - make sure they know S-Corp rules inside and out). We did a full reconstruction of my books going back to the S-Corp election date. The salary issue is critical - you need to get on payroll ASAP. My CPA calculated what my reasonable salary should have been from day one and we did retroactive payroll for the entire period. Yes, I had to pay employment taxes on that amount, but it protected me from much worse penalties if the IRS had discovered it first. One thing that really helped was creating a detailed memo explaining the situation, the steps we took to fix it, and the controls we put in place to prevent it from happening again. Documentation is your friend here. The good news is that the IRS sees this mistake frequently with new S-Corps, and they're generally reasonable if you proactively fix it and can show you took it seriously. Don't let the fear paralyze you - take action now and you'll sleep much better in a few months.