For missing records, you might also want to check if your company had a transfer agent that kept historical records. Many older stocks were managed by companies like Computershare or AST Financial Services, and they sometimes have records going back decades. If you can establish the original number of shares and approximate purchase date, you can work backwards through all the corporate actions (splits, spinoffs, etc.) to determine what you should have today. The key is documenting your methodology in case the IRS ever questions it. I had a similar situation with some old utility stocks from the 80s where I'd lost the original paperwork. I was able to reconstruct the cost basis by finding the stock's historical prices and applying all the subsequent splits and dividend reinvestments. It took some detective work, but it's definitely doable with patience.

I went through something very similar with my old Coca-Cola shares that I inherited and had in DRIP for years. The key thing to remember is that each DRIP purchase creates a separate tax lot with its own cost basis and purchase date, even if it's just buying a fraction of a share. For record-keeping, I'd strongly recommend creating a spreadsheet that tracks each purchase (including reinvested dividends) with the date, number of shares purchased, and price per share. Then apply any stock splits chronologically to adjust both the share count and cost basis per share for each lot. When you sell using FIFO, you're correct that you'd start with your oldest shares first. So yes, your original gifted share (now 4 shares after the splits) would be sold first, then move chronologically through your DRIP purchases. One thing to watch out for: make sure you're accounting for any dividend reinvestments that happened between the stock splits, as those would have their own purchase dates and would also be subject to the split adjustments. It can get complex quickly, but the principle remains the same - oldest shares out first under FIFO.

I'm dealing with a similar situation with my vacation rental and this thread has been incredibly helpful! Based on what I'm reading, it sounds like the key is first determining whether your property falls under the 7-day rule (making it a business activity) or if it's a traditional rental activity. For traditional rental activities with longer average stays, the active vs passive participation distinction matters a lot for the $25,000 loss allowance. But for short-term rentals with average stays of 7 days or less, you're looking at material participation tests instead since it's considered a business activity. One question I still have - if you have multiple short-term rental properties, do you evaluate the participation tests for each property individually, or can you combine your activities across all properties? I manage three different Airbnb units and I'm not sure if my management time gets pooled together or evaluated separately for each property.

This is such a helpful discussion! I'm in a similar boat with my mountain cabin rental and the distinction between active vs passive participation has been driving me nuts too. What really helped me was tracking all my management activities in detail - even the time spent reviewing financial reports, approving repairs, and communicating with the property management company. I realized I was doing way more "active participation" work than I initially thought. One thing I learned the hard way is that the average rental period calculation is crucial. My cabin has some week-long rentals mixed with weekend stays, so I had to carefully calculate the average to determine if the 7-day rule applied. It turned out my average was 8 days, so I stayed in the traditional rental activity category where active participation mattered for the $25k loss allowance. The income phase-out is also something to watch carefully - if you're close to that $100k-$150k range, it might be worth timing some income or deductions to maximize your rental loss deduction eligibility.

I'm confused about one thing - if the apartment is outside the US, don't you have to report it on FBAR and Form 8938 regardless of whether it's rental or personal? My accountant told me all foreign properties need to be disclosed even if they don't generate income.

This is a really complex situation that highlights how confusing tax software can be with edge cases. You're absolutely right that TurboTax should have caught this - when you entered "0" for both fair rental days and personal use days, that's mathematically impossible since the property exists somewhere for 365 days. Based on what others have explained here, it sounds like you need to go back and correct your filing. You should enter 365 days for personal use (since below-market rentals to friends/family are considered personal use), which would take you out of the Schedule E rental property track entirely. The good news is that if your maintenance fees are less than your property taxes, you likely don't need to report any income at all. But you should definitely get professional help or use one of the tools mentioned here to make sure you're handling the foreign aspects correctly - there are additional considerations for foreign properties that go beyond just the rental vs. personal determination. Don't feel bad about the confusion - this is one of those areas where the tax code is genuinely unclear and even tax professionals sometimes get it wrong!

Great question about LLC conversions! I've handled several similar situations and wanted to add a few practical considerations: Regarding your timing question - the 12/31/24 effective date approach is definitely the cleaner route administratively. You're right that it avoids the complexity of short-year returns, and since your partner has 0% allocation anyway, there's no meaningful tax difference between the dates. One thing to watch out for: make sure your operating agreement doesn't have any specific termination procedures that need to be followed when a member exits. Some agreements require formal notice periods or buyout procedures, even for members with minimal stakes. Also, consider having the exiting partner sign a release agreement as part of the conversion process. Even though they have no financial stake, this protects against future claims and provides clean documentation for your records. For the Airbnb property specifically - verify that the property deed and any related financing documents won't need updates when the LLC converts to single-member. Some lenders have clauses about ownership changes that could be triggered. The conversion process itself is usually straightforward, but the documentation cleanup often takes longer than expected. Start gathering all your LLC formation documents, operating agreements, and any amendments now so you're ready when you file the 8832.

I've been through a similar conversion process and wanted to share some additional insights based on my experience: For your Form 8832 timing question, I'd actually lean toward the 12/31/24 effective date as well. The administrative simplicity of avoiding short-year returns usually outweighs any minor benefits of an earlier conversion date, especially when the partner has 0% allocation anyway. One thing I learned the hard way - make sure to update your EIN situation properly. When you convert to SMLLC, you'll generally keep the same EIN, but some banks and vendors get confused about the entity status change. I recommend sending updated W-9s to all your business contacts after the conversion to avoid 1099 reporting issues. Regarding the retroactive ownership agreement in point #3 - I'd strongly advise against this approach. Instead, consider having the partner execute a formal assignment of their membership interest (even if valued at $0) to your client with current dating. This maintains the integrity of your historical records while achieving the same practical result. Also, don't forget about your state's annual report requirements. Some states require you to file an amendment or updated report when membership changes, even for conversions like this. The penalties for missing these filings can be surprisingly steep. Have you considered whether any business licenses or permits might need updating after the conversion? Some licensing authorities treat SMLLC differently than partnerships, especially for rental properties.

Has anyone used the corporate credit card approach? My accountant suggested getting a separate credit card for my S-Corp, putting all client-reimbursable expenses on that card, and then recording the reimbursements as direct payments against those specific expenses in my accounting software rather than as income.

This thread has been incredibly helpful! I'm in a similar situation as the original poster - just converted to S-Corp this year and have been struggling with how to handle client meal reimbursements properly. One thing I wanted to add that might help others: make sure you're keeping contemporaneous records of the business purpose for each meal. The IRS requires documentation of who you met with, what business was discussed, and the specific business relationship. Even with client reimbursement, you still need this documentation to support that it was a legitimate business expense in the first place. I learned this the hard way when my previous accountant told me I just needed receipts, but during a review, I realized I was missing the business purpose documentation for about half my meals. Had to go back through old calendars and emails to reconstruct what each meal was for. Now I write the business purpose right on the receipt when I get it, or immediately add it to my expense tracking app. Also, for anyone using the separate credit card approach that @Zoe mentioned - make sure that card is officially in your S-Corp's name, not just a personal card you designate for business use. The legal separation is important for maintaining your corporate protections.