Has anyone here actually gone through with a large Roth conversion in a low income year? I'm considering doing about $35k conversion but I'm worried I'll regret it when tax time comes.

This is exactly the kind of situation where proper tax planning can save you thousands! With your $41k income and massive capital losses, you're actually in a unique position. While those losses can't directly offset Roth conversion income (as others mentioned), your low current income means you're in a great tax bracket for conversions. I'd strongly recommend running the numbers on converting enough to fill up your 12% tax bracket - probably around $8k based on your current income. Even though you'll pay taxes on the conversion, you're essentially "prepaying" taxes at today's lower rates rather than potentially higher rates in retirement. The key insight here is that your capital losses will carry forward for years, giving you ongoing $3k annual deductions against ordinary income. This means your effective tax rate might be even lower than the bracket suggests. Don't let the losses go to waste - use this low-income year strategically for tax-advantaged growth!

Just a heads up - make sure you're tracking the "unadjusted basis" correctly. This should be the original cost of the building portion only (not including land) before any depreciation. For an inherited property, it would typically be the fair market value of the building (not including land) at the time of inheritance. So if your property is worth $320k total but $50k of that is land value, your building basis would be $270k, making the 2% threshold $5,400. That would be lower than the $10k cap, so $5,400 would be your safe harbor limit.

This is such a helpful thread! I'm dealing with a similar situation with my rental property. One thing I want to add is that documentation becomes really important when you're near or over the safe harbor limits. I learned this the hard way during an audit a few years ago - the IRS agent wanted detailed records showing exactly what work was done and why it was necessary. For repairs like your HVAC replacement, having documentation that the old system was broken/non-functional (like repair estimates or photos) really helps support the "repair" classification versus "improvement." Also, timing can matter. If you're close to your safe harbor limit and have discretionary maintenance work planned, you might consider spreading it across tax years to stay under the threshold when possible. Obviously you can't delay emergency repairs like your mold situation, but things like painting or minor updates could potentially be timed strategically. The inherited property basis calculation mentioned above is spot on - make sure you're using the stepped-up basis correctly and allocating between land and building properly. A good appraisal from the time of inheritance can be invaluable for this.

Just a tip from my experience - if you file as "Married Filing Separately" without getting an ITIN for your spouse this year, but later decide you want to amend to "Married Filing Jointly" after getting their ITIN, you CAN do this! You have 3 years from the original filing deadline to file an amended return.

I was in almost the exact same situation two years ago - J1 visa with a J2 spouse who had no SSN or ITIN and zero income. Here's what I learned: The key decision is whether the potential tax savings from filing jointly justify the hassle of getting an ITIN for your spouse. Since you mentioned having just one W2, if your income is relatively modest, the difference between the MFS standard deduction ($13,850) and MFJ standard deduction ($27,700) could save you significant money. However, getting an ITIN can take 6-11 weeks during tax season, and you'd need to mail your original passport or certified copies along with Form W-7. If you're not comfortable mailing your passport, you can visit an IRS Taxpayer Assistance Center, but appointments are hard to get. For your first year, I'd honestly recommend starting with MFS to get your return filed on time, then consider getting the ITIN for next year when you have more time to plan. You can always amend later if the tax savings are worth it, but at least you won't miss any deadlines while waiting for ITIN processing. Also, make sure you're claiming any applicable tax treaty benefits - many J1 visa holders from certain countries can exempt part of their income for the first few years.

Has anyone used any of the major tax software programs to handle this specific situation? I'm trying to use TurboTax for a similar issue with GoFundMe medical expenses and can't figure out where to even indicate that some expenses were paid through donations.

This is such a tough situation to navigate, and I feel for your sister dealing with this on top of everything else. Just wanted to add one important point that might help - make sure she keeps detailed records separating what was paid from GoFundMe vs. what came out of pocket, even if she can't deduct the GoFundMe portion. The IRS can be pretty strict about documentation if they ever audit medical expenses, so having clear records showing the source of each payment will be crucial. I'd suggest creating a simple spreadsheet with columns for date, expense description, total amount, GoFundMe portion, and out-of-pocket portion. Also, don't forget about smaller medical expenses that might have been paid directly - things like prescription copays, parking fees at the hospital, or travel expenses for treatment. These add up and are often overlooked but can be deductible if paid from personal funds. Hope your niece continues to respond well to treatment. The tax stuff is complicated but manageable with good record-keeping!

This is such an eye-opening thread! I had no idea this kind of mix-up was so common with commercial property taxes. Reading through everyone's experiences, it sounds like there are several key takeaways for small business owners: 1. **Always verify who should be receiving tax bills** - Even with triple net leases, the bills typically should go to the landlord first, not directly to tenants 2. **Calculate your proportionate share** - If you're in a multi-tenant building, make sure you're only paying for your actual square footage percentage 3. **Document everything** - Keep copies of leases, payments, and all correspondence for potential refund claims 4. **Act quickly** - Most counties have time limits on how far back you can claim refunds For anyone just discovering they might be in this situation, it seems like the combination of reviewing your lease terms + contacting the county assessor's office + potentially using services like those mentioned by other members could save thousands of dollars. Thanks to everyone who shared their experiences and solutions - this is exactly the kind of community knowledge sharing that helps small business owners avoid costly mistakes!

Wow, reading through this thread has been incredibly enlightening! As a fellow small business owner, I had no idea how common these property tax mix-ups are in commercial leasing situations. I'm currently renting a small retail space and now I'm wondering if I should double-check my own situation. My lease mentions something about "additional rent for taxes" but I've never received direct tax bills from the county - everything goes through my landlord and gets added to my monthly rent statement. After reading all these experiences, it sounds like that's actually how it SHOULD work, which makes me feel better. But it's concerning how many business owners have been caught off guard by direct tax bills when they should have been going through the property owner. The professional advice from @Samantha Johnson about the data entry errors during business registration really explains a lot. It makes me think counties should have better systems in place to distinguish between business registrations and actual property ownership transfers. For @Ravi Sharma - definitely pursue getting those refunds for your previous overpayments! Based on what others have shared, it sounds like you have a strong case, especially for the old location you vacated months ago. The combination of lease documentation + move-out proof should be pretty compelling evidence for the county assessor's office. Thanks to everyone for sharing their experiences and solutions - this is exactly the kind of community knowledge that helps prevent other small business owners from falling into the same expensive trap!