Has anyone used withdrawals from a Health Savings Account (HSA) for vehicle modifications? I know HSAs can be used for qualified medical expenses tax-free, but I'm not sure if vehicle mods count the same way they do for regular tax deductions.

I'm going through something very similar with my daughter who needs a specialized wheelchair van. One thing I discovered that might help is to also check if your son qualifies for any state vocational rehabilitation services. In many states, if the vehicle modifications help with independence or potential future employment, vocational rehab will cover a significant portion of the costs. Also, definitely keep detailed records of everything - not just the modification costs, but also any medical documentation from your son's doctors stating the medical necessity for the accessible vehicle. I learned the hard way that the IRS wants clear medical justification, not just receipts. For the 401k withdrawal, make sure you understand the timing. You can only use the medical expense exception for unreimbursed medical expenses in the same year as the withdrawal. So if you withdraw in 2025, the medical expenses need to be from 2025 to qualify for the penalty exception. Have you considered financing through the modification company? Many offer medical financing with lower interest rates than what you'd lose by early 401k withdrawal. Sometimes the monthly payments are more manageable than the tax hit from a large withdrawal.

Don't forget to look into college financial aid too! When my daughter started college, we discovered that how we claimed her on taxes affected her FAFSA application. Sometimes the tax benefits vs. financial aid benefits can be a tradeoff.

I'm going through this exact transition right now with my oldest! One thing that really helped me plan was creating a simple spreadsheet to compare the financial impact year by year. For 2024 taxes (filed in 2025): You'll still get the full Child Tax Credit since she's 17 at year-end. For 2025 taxes (filed in 2026): No more Child Tax Credit, but if she's in college full-time, you can still claim her as a dependent AND potentially get the American Opportunity Tax Credit (up to $2,500 for the first 4 years of college). The key thing is that "providing more than half her support" - keep track of what you spend on her (tuition, room/board, food, medical, etc.) vs. any income she earns. As long as your support exceeds 50% of her total support for the year, you can claim her. Also, don't forget that claiming her as a dependent might affect her eligibility for certain financial aid, so definitely talk to the college financial aid office before making decisions. Sometimes it's better for the student to file independently depending on the aid packages available. The transition definitely stings financially, but the education credits can help bridge some of that gap if she goes to college!

This thread has been incredibly helpful! I'm a tax preparer and I see situations like yours all the time, especially with clients who have investment properties and primary residences. One thing I always tell my clients in your situation is to create a simple timeline document showing: (1) when you took out the HELOC, (2) when you used the funds for the home purchase, and (3) how much was used. This makes it much easier to explain to the IRS if you ever get questioned. Also, since your duplex is now fully rental, don't forget that you might be able to deduct other expenses related to that property on Schedule E - property management fees, repairs, depreciation, etc. The HELOC interest allocation is just one piece of optimizing your tax situation with multiple properties. Keep all those closing documents and bank statements showing the money trail from HELOC to home purchase. The IRS loves a clear paper trail, and it sounds like you're in good shape for claiming that deduction!

Great question! I went through almost the exact same situation last year. You're definitely on the right track - the key is that you used the HELOC proceeds to acquire your primary residence, which makes that interest potentially deductible under the current tax rules. Just to echo what others have said, the IRS traces how the loan funds were actually used rather than just looking at which property secures the loan. Since you used your duplex HELOC to buy what became your primary residence, that interest should qualify for the mortgage interest deduction on Schedule A. One thing I'd add is to make sure you understand how this affects your overall tax picture. The duplex mortgage interest (not the HELOC portion) will now be a rental expense on Schedule E since it's fully a rental property. But the HELOC interest goes on Schedule A as personal mortgage interest because of how those funds were used. I kept a simple folder with my closing statement from the house purchase, the HELOC agreement, and bank statements showing the fund transfers. Made tax prep much smoother and gave me confidence I could back up the deduction if needed. Sounds like you're in good shape with your documentation!

Based on what you've described, you'll likely need to file as Single rather than Head of Household. Since your mom makes around $25,000, she fails the gross income test for being claimed as your dependent (the limit is $4,950 for 2024), which means you can't use her to qualify for HoH status. However, don't let that discourage you from keeping good records! Even though you can't claim the tax benefits this year, documenting all your expenses is still valuable. Keep those bank statements showing rent and utility payments, grocery receipts, and any other household expenses you cover. If your mom's work situation changes in the future - reduced hours, job loss, retirement - and her income drops below that threshold, you'll already have a solid documentation system in place. For this year, make sure you're maximizing other tax benefits available to Single filers. Don't forget about the student loan interest deduction (up to $2,500), contributions to traditional IRAs or 401(k)s, and any education credits if you're taking classes. The standard deduction for Single filers is $13,850 for 2024, which is likely your best option unless you have significant itemizable deductions. It's frustrating when you're clearly supporting someone but can't get the tax recognition for it, but you're doing the right thing by researching this carefully rather than just assuming you qualify.

I appreciate everyone sharing their experiences and resources! Just to add one more perspective - I went through this exact situation two years ago with my disabled brother who was receiving SSDI benefits. Even though you can't claim HOH status this year due to your mom's income, don't overlook the emotional and practical value of what you're doing. Supporting a family member is significant even without the tax benefits. One thing that helped me was setting up a simple spreadsheet to track shared expenses from the beginning of each tax year - rent, utilities, groceries, medical costs, everything. I included columns for what I paid vs. what my brother contributed. This made it crystal clear what percentage of support I was providing, which was useful not just for taxes but also for my own budgeting. Also, since you mentioned this is your first year doing taxes on your own, consider using the IRS Free File program if your income qualifies. Even though you'll be filing as Single, the guided interview process can help ensure you're not missing any deductions or credits you're eligible for. The software will walk you through questions about student loan interest, retirement contributions, education expenses, and other potential tax benefits. Keep those records organized - you're building a great foundation for future years when circumstances might change!

Has anyone tried just using the IRS e-file system instead of faxing? I've submitted most of my documents electronically through their portals and haven't needed to fax anything for the past two years.

I've been using RingCentral Fax for sending documents to the IRS and it's been solid. What I really like about it is that they provide detailed transmission reports that include not just delivery confirmation, but also the exact time stamps and even the quality of the transmission. One thing I learned the hard way - always double-check the IRS fax number you're sending to. Different departments have different fax numbers, and I once sent my documents to the wrong one and had to resend everything. The IRS website has a directory of fax numbers by department and form type. Also, if you're sending multiple pages, I'd recommend calling the IRS first to confirm they received everything. Even with confirmation receipts, pages can sometimes get separated or lost in their system. Better to verify than to find out months later that they're missing page 3 of your submission!