Has anyone tried claiming the tutoring costs as Miscellaneous Itemized Deductions instead of medical expenses? I read somewhere that educational therapy might qualify that way and then you wouldn't have to hit that 7.5% AGI threshold.

I'm dealing with a similar situation for my daughter who has ADHD. One thing I learned from our experience is that you'll want to make sure your reading specialist is qualified to provide services for learning disabilities - the IRS may scrutinize whether the provider has appropriate credentials to treat the specific condition. Also, don't forget that you can potentially include related expenses like mileage to and from tutoring sessions (currently 22 cents per mile for medical travel in 2023). If you're paying $725 per month and driving to sessions regularly, those transportation costs can add up to a meaningful additional deduction. Keep detailed records of everything - session dates, payments, progress notes if the tutor provides them. The more documentation you have showing this is legitimate medical treatment rather than general academic support, the better positioned you'll be if questions arise.

17 Could just paper file. It's free and the processing time isn't really that bad anymore. I mailed in a 1041 last month and got the confirmation within 3 weeks. Just make sure to send it certified mail so you have proof of delivery.

Another option to consider is FreeTaxUSA, which typically charges around $50-70 for Form 1041 filing - much more reasonable than TurboTax's $199. I used them for my grandmother's estate return last year and found their 1041 interface straightforward enough, especially since you already have your forms completed. If you're looking for the absolute cheapest route and aren't in a rush, paper filing really isn't that bad. The IRS has actually improved their processing times significantly. Just make copies of everything, send it certified mail, and you'll save the e-filing fees entirely. The trade-off is waiting a bit longer for confirmation, but for a straightforward estate return it's often worth the savings.

I've been following this thread and wanted to add some clarity from my experience as someone who's dealt with this exact situation multiple times. The confusion often comes from how partnership taxation works versus how IRA contribution eligibility is determined. Here's the key distinction: guaranteed payments to partners are reported on your K-1 (Box 4) and represent compensation for services you provided to the partnership. Even though these payments get combined with your share of partnership income/loss on Schedule E, they don't lose their character as "earned income" for IRA purposes. Think of it this way - if you work for a corporation and receive a W-2 salary, but the corporation loses money, your salary is still earned income for Roth contributions. Guaranteed payments work similarly - they're compensation for your services, separate from your ownership interest in the partnership's profits or losses. The IRS specifically addresses this in Publication 590-A under the definition of compensation. As long as your guaranteed payments were for services (not for use of capital), they count toward your Roth contribution limit regardless of whether the partnership had a net loss. So with your $26,500 in guaranteed payments, you should be able to contribute up to the annual Roth IRA limit, assuming you meet the income phase-out requirements.

This is such a common misconception that trips up so many partnership taxpayers! I went through this exact same situation a few years ago and initially thought I couldn't contribute to my Roth because my Schedule E showed a net loss. The key insight that finally clicked for me is that guaranteed payments maintain their character as compensation regardless of what happens with the rest of the partnership's operations. It's almost like having two separate tax events - you received compensation for services (the guaranteed payments), and separately, your ownership interest in the partnership experienced a loss. I'd strongly recommend double-checking with a tax professional who understands partnership taxation, because this is an area where many general practitioners get confused. The IRS publications are pretty clear on this, but it's easy to miss if you're just looking at the bottom-line numbers on your tax return. With $26,500 in guaranteed payments, you should definitely be able to make your Roth contribution (assuming you're under the income phase-out limits). Don't let a partnership loss cost you a whole year of retirement savings!

Just wanted to add - make sure you keep copies of EVERYTHING related to your nondeductible contributions forever (or at least until you've withdrawn all the money). I learned this the hard way. I had made nondeductible contributions years ago, filed my 8606 forms properly, but then lost track of the paperwork during a move. When I started taking distributions years later, I couldn't prove my basis to the IRS and ended up paying tax on money that should have been tax-free coming out. The burden of proof is 100% on you to track your nondeductible basis, not on the IRS. They don't keep easily accessible records of your basis year to year.

Great advice from everyone here! I went through this exact situation last year when I discovered I had missed filing Form 8606 for multiple years of nondeductible contributions. One thing I'd add that helped me tremendously - when you mail your Form 8606, use certified mail with return receipt requested. The IRS can be slow to process these forms, and having proof of delivery gives you documentation that you filed it timely (even though it's late for the original tax year). Also, consider keeping a detailed log of all your IRA transactions going forward. I created a simple spreadsheet that tracks: - Date of contribution - Amount contributed - Tax year it applies to - Whether it was deductible or nondeductible - Form 8606 filing status This has made my annual tax prep so much easier and ensures I never miss tracking my basis again. The few hours spent organizing this information upfront saves tons of stress later, especially if you ever need to prove your basis to the IRS during an audit or when taking distributions. Your numbers look correct for the 2022 form, and yes, you should include the full $15,500 basis on your 2023 Form 8606 even if the 2022 form hasn't been processed yet. The key is that you're filing it before or with your 2023 return.

As someone who's been through the audit process, I want to emphasize what Natasha said about documentation. Even if you had a qualifying medical expense, the IRS will want extensive documentation during an audit - not just a doctor's note, but detailed records showing the medical necessity, treatment plan, and how the expense specifically addresses your diagnosed condition. For your Planet Fitness situation, even if you kept perfect records, the fundamental issue is that general gym memberships don't qualify regardless of medical recommendation. The IRS has consistently ruled that these are personal expenses for general health maintenance. One thing I learned the hard way: it's better to miss a legitimate deduction than to claim a questionable one. The stress and cost of dealing with an audit far outweigh the tax savings from a gym membership deduction. Focus on the clear-cut deductions for your freelance business instead - those are much more valuable and defensible.

This thread has been incredibly helpful! As someone who's also self-employed and was wondering about similar deductions, I really appreciate all the detailed explanations from the tax professionals here. I've been making the same mistake of thinking that anything health-related recommended by a doctor might be deductible. The distinction between "general health maintenance" vs "treatment of a specific condition with qualified medical personnel" that Natasha explained really cleared things up for me. It's also eye-opening to learn about the 7.5% AGI threshold - I had no idea medical deductions had such a high bar to clear before they even start helping. Between that and the standard deduction being so high, it sounds like most of us probably won't benefit from medical expense deductions anyway. Thanks everyone for sharing your experiences and expertise. This community is so much more helpful than trying to wade through confusing IRS publications on my own!