Don't forget you can also deduct state and local taxes (SALT) up to $10,000 when itemizing! This includes state income tax or sales tax (you choose which one), plus property taxes. If you paid state income tax through withholding from your paycheck, that counts toward this potential deduction. Even if your medical expenses aren't enough by themselves to exceed the standard deduction, combining them with SALT deductions might push you over the edge. Check your W-2 box 17 to see how much state tax was withheld, and add any property taxes if you paid them.

One thing to consider - if youre close to making itemizing worth it, donating some stuff to charity before the end of the year could push u over the edge! I was in a similar spot last year and cleaned out my closet, got a receipt from Goodwill for like $350 in donated clothes and that was enough to make itemizing better than standard deduction for me.

Quick tip for anyone filing back taxes with ITIN/SSN issues - print out copies of everything before you mail it! My returns got "lost" twice and having copies saved me from having to redo all that work. Also consider paying for tracking when you mail returns to the IRS.

I went through almost the exact same situation last year! My husband transitioned from ITIN to SSN in 2022, and we had to file back taxes for 2018-2020. Here's what I learned from working with a tax professional: 1. Use the ITIN for those tax years (2019-2020) since that's what was valid then 2. Make sure to check if the ITIN was still valid for those years - if it expired, you'll need to renew it first 3. Include a cover letter explaining the ID number change to avoid processing delays 4. You're right that you won't qualify for certain credits like EIC for those years, but that's unfortunately how the system works For the payment plan, make sure all your returns are filed and processed first. The IRS won't approve a payment plan until they have all required returns on file. Once everything is processed, you can apply online if you owe less than $50K total. One thing that helped us was getting a tax transcript for each year to confirm our returns were properly processed before applying for the payment plan. You can request these online through the IRS website. Good luck - I know how stressful this whole process is, but you'll get through it!

I'm dealing with a very similar situation right now - temporarily relocated to help care for my spouse's mother while renting out our primary home. One resource that's been incredibly helpful is the IRS Taxpayer Advocate Service, especially if you run into any issues or need clarification on complex scenarios like ours. What I've learned through this process is that the key is meticulous record-keeping from day one. Beyond what others have mentioned about rental expenses and active participation, I'd also suggest: - Keep copies of any medical documentation related to your parents' care needs - Document your voting registration, driver's license address, and any other ties to your primary residence - Save utility bills, insurance policies, and other documents that show your intent to return - Keep records of any home improvements or maintenance you do remotely One thing that surprised me was learning about the "unforeseen circumstances" provisions in tax law. If your temporary situation extends beyond what you originally planned due to your parents' changing health needs, there are sometimes additional protections for primary residence status. The emotional stress of caring for aging parents is hard enough without worrying about tax complications. Just remember that you're doing the right thing, and the tax code generally recognizes these kinds of family care situations as legitimate reasons for temporary relocation. The documentation might seem excessive now, but it provides peace of mind if any questions come up later.

I've been following this thread with great interest as I'm in an almost identical situation - temporarily relocated to care for my aging mother while renting out our primary home. The discussion here has been incredibly helpful, especially the points about active participation and the potential for rental losses to actually provide tax benefits. One additional consideration I'd like to add is about timing your return strategically. If you're approaching the end of a tax year and have flexibility in when you move back, it might be worth consulting with a tax professional about whether returning in December vs. January could impact your overall tax situation, especially regarding the rental loss deductions and primary residence status. Also, for anyone using property management software or apps to coordinate with tenants remotely, keep screenshots and records of your management activities. I use a simple rental management app that tracks all my communications with tenants, maintenance requests, and rent collection - this documentation has been invaluable for establishing active participation. The emotional toll of managing a rental property while caring for elderly parents is real, but this thread has shown me there are more tax advantages to our situation than I initially realized. Thanks to everyone who has shared their experiences and resources - it's made a stressful situation much more manageable.

One additional consideration that hasn't been fully addressed - if you're dealing with significant investment gains, you might want to explore charitable remainder trusts (CRTs) or donor-advised funds as alternatives to direct donations. With a CRT, you could transfer some of your appreciated stock directly to the trust, get an immediate charitable deduction, avoid capital gains tax on the transfer, and still receive income payments back over time. This could be especially beneficial given your unexpected investment returns. Donor-advised funds are simpler and let you make a large contribution in a high-income year (like this one with your investment gains), get the immediate tax deduction if you itemize, and then distribute the funds to charities over multiple years. You'd still need to itemize to benefit, but it gives you more flexibility in timing your charitable giving. Since you're in a partnership, these strategies would typically be done personally rather than through the LLC, but they might be more tax-efficient ways to achieve your charitable and tax planning goals given your current situation with the investment gains.

This has been such a helpful thread! As someone also dealing with unexpected investment gains in my LLC partnership, I wanted to share what I learned after consulting with a tax specialist following this discussion. The key insight was that LLC charitable donations are really more about the individual partners' tax situations than the business itself. Since the deduction passes through, it only helps if you itemize - and with the current high standard deduction amounts, many people don't. What worked better for my situation was a hybrid approach: 1) Used legitimate business expenses (equipment purchases, professional development) to reduce the partnership income directly 2) Made personal charitable donations using the stock donation strategy mentioned by Nia - donated appreciated shares directly to avoid capital gains while getting the full FMV deduction 3) Bunched two years of planned donations into this high-income year to push itemized deductions above the standard deduction threshold This combination gave us both business-level tax reduction AND personal charitable deductions that actually provided tax benefit. The stock donation piece was especially powerful since we avoided paying capital gains on the appreciation. For anyone in a similar situation, I'd definitely recommend mapping out both business expense strategies AND personal charitable giving strategies rather than assuming business donations are automatically better. The pass-through nature of partnerships makes the tax planning more nuanced than it first appears.

write down everything they tell you! I always forget important details after the call smh

stuck on hold rn actually...going on 47 minutes 😭