22 Can someone explain what happens with the depreciation you've taken when you sell at a loss? I know if you sell at a gain, there's depreciation recapture, but what if you're already taking a loss?

This is a really comprehensive discussion about converted rental properties! I'm dealing with a similar situation where I converted my primary residence to a rental in 2021. One thing I'd add is that you should also keep detailed records of any improvements you made to the property both before and after conversion. Capital improvements made while it was your primary residence get added to your original basis, while improvements made after conversion to rental property are treated differently - they create separate depreciable assets with their own recovery periods. This can actually help reduce your taxable loss or increase your deductible loss depending on the timing. Also, don't forget about the home office deduction if you used part of your primary residence for business before converting it - that creates yet another layer of complexity in the basis calculations. I learned this the hard way when preparing my taxes last year!

I used to be a bartender and now I do tax prep, and I see this issue from both sides. From the venue perspective, we had several "social media influencers" who would come in and drink while filming. The IRS would definitely consider this a legitimate business expense IF (big if) you're actually generating revenue from these streams. The test is: would a reasonable businessperson in your industry consider this an ordinary and necessary expense? For nightlife content? Absolutely yes.

This is a fascinating tax situation that highlights how modern content creation businesses push the boundaries of traditional tax categories. Based on what you've described, I believe you have a strong case for deducting these expenses. The critical factor here is that the alcohol serves a legitimate business purpose - it's essentially a required element of your content, similar to how a food blogger needs to purchase ingredients or a makeup artist needs cosmetics. Since you've stated that you never visit these establishments for personal reasons and only consume alcohol while creating content, you've established clear business purpose. I'd recommend treating these as "production costs" or "content creation materials" rather than meals & entertainment to avoid the 50% limitation. However, be prepared with rock-solid documentation: detailed receipts, stream links, business purpose notes, and ideally separate business payment methods. One thing to consider - since this represents $8,000 annually, you might want to consult with a tax professional who has experience with content creator businesses before filing. The unique nature of your business model means you want to ensure you're categorizing everything correctly to minimize audit risk while maximizing legitimate deductions. The fact that you've been conservative for 3 years actually works in your favor - it shows you're not trying to push questionable deductions, just properly claiming legitimate business expenses as you've learned more about tax law.

There's one thing nobody's mentioned yet that could be significant. If you DO amend as married filing jointly, be aware that both partners become jointly liable for the entire tax amount. This means if there are any issues with either person's reporting, both could be on the hook. Given the income disparity ($25-40k vs $470-950k), you might want to consider whether married filing separately might actually be better in some years than joint filing. Sometimes with very disparate incomes, the tax savings of joint filing aren't as large as you might expect. Also, think about whether you're planning to get formally married in the future. If you establish common law marriage for tax purposes now, you'd technically need a formal divorce if you ever split up, even without having had a wedding ceremony.

This is a fascinating case study in tax strategy! As someone who's dealt with complex filing situations, I'd strongly recommend getting professional help before proceeding, but your logic seems sound. One thing to consider: with your income levels, you'll want to run the numbers carefully for each year. Sometimes when one spouse has very high income and the other has low income, married filing jointly provides substantial savings due to income averaging effects, but other years it might not be as beneficial as expected due to phase-outs of deductions and credits. Also, keep in mind that amending returns of this magnitude will likely trigger enhanced scrutiny from the IRS. They'll want bulletproof documentation not just of your common law marriage status, but also of when exactly you became common law married. The July 2018 date when you moved to SC and merged finances will be critical - you'll need to show clear evidence that your relationship status changed at that specific time. Document everything: bank account opening dates, when you were added to health insurance, property records, any legal documents from that timeframe. The IRS will be looking for consistency in your story and timeline. Given the potential six-figure recovery, investing in quality legal and tax professional advice upfront could save you significant headaches later. Good luck!

I went through this exact same situation with my company's RSUs last year! The key thing to understand is that your 1099-B is only showing the transaction for the 83 shares that were sold to cover taxes, not all 220 shares that vested. Here's what's happening: When your 220 RSUs vested in August 2024, the full $53,130 ($241.50 × 220) was added to your W-2 as ordinary income and you were taxed on it. Your company then sold 83 shares at $238.75 each to cover the $19,810.50 in taxes. The 1099-B shows this sale of 83 shares, with proceeds of $19,810.50 and a cost basis of $20,025.25. The cost basis being slightly higher than the proceeds means you actually have a small capital loss of about $214.75 on those shares sold for taxes. For the 137 shares you kept, your cost basis is $241.50 per share (the FMV at vesting). These shares don't appear on any 1099-B until you actually sell them. When filing your taxes, you'll need to report the 1099-B transaction but make sure to indicate that the compensation element was already included in your W-2 to avoid double taxation. Most tax software will handle this automatically when you enter both your W-2 and 1099-B information. The fact that your brokerage doesn't have additional documentation is unfortunately normal - the 1099-B is all they're required to provide.

One additional tip that might help for future reference - I always recommend downloading and saving your RSU release documents immediately when they vest. Companies sometimes change brokerages or systems, and those detailed vest confirmations can be harder to access later. Also, if you have multiple RSU grants or future vests, consider setting up a simple tracking system now. I use a basic spreadsheet with columns for vest date, shares vested, FMV at vest, shares sold for taxes, and remaining shares. It makes tax time so much easier when you have everything organized in one place. The IRS has been cracking down on unreported stock compensation lately, so having good records is more important than ever. Your situation sounds straightforward now that others have explained it, but having that documentation trail will be valuable if you ever get audited or have questions in future years.

This might sound dumb, but I've found that the easiest way to check YTD accuracy is to just add up all your paystubs manually. Companies mess this up more than ppl realize. At my last job, the YTD on my stub was wrong for 3 months and nobody noticed until I pointed it out! They had a system change and some paychecks weren't being counted in YTD.

Dylan, looking at your numbers, I think the mystery might be simpler than you think. You mentioned getting a "small bonus" when you started - that's almost certainly what's throwing off your calculation. If your YTD shows $13,541.65 and your regular pay is $2,708.33 per paycheck, then: $13,541.65 ÷ $2,708.33 = 5.0 exactly This means your YTD includes exactly 5 "paycheck equivalents" worth of income. Since you said you've only received 4 regular paychecks, that extra $2,708.33 is likely your sign-on bonus. Even if the bonus seemed "small" to you, it might have been grossed up for taxes (meaning they paid extra to cover the tax burden), or there could have been other compensation included like relocation assistance, referral bonuses, etc. Check your very first paystub of the year - you'll probably see the bonus listed there as a separate line item, but it's still included in your gross pay and YTD calculations. That would explain why your math is off by exactly one paycheck amount.