I'm in a very similar situation with my Solo 401k! Set it up years ago through Schwab and only recently discovered all the compliance requirements I've been missing. The amount of technical details around plan documents, amendments, and filing requirements is honestly overwhelming. One thing I learned during my research is that even if your plan balance is under $250k, you still need to maintain proper plan documentation and stay current with regulatory changes. The brokerage firms really don't make this clear when you set up the account - they focus on the investment side but leave you hanging on the administrative compliance. I'm definitely going to look into some of the TPA recommendations mentioned here. The peace of mind alone would be worth the annual cost, especially knowing that retirement plan audits can go back several years. Better to get everything properly documented now than deal with potential issues later when we're ready to start taking distributions. Thanks for starting this thread - it's reassuring to know I'm not the only one who was caught off guard by all these requirements!

I completely understand your situation - this is actually much more common than you'd think! I've been working with Solo 401k plans for several years now, and the confusion around compliance requirements is something I see regularly. First off, don't panic about the missed Form 5500 filings. The fact that you've already self-corrected those puts you in a much better position than many people who discover this issue. The IRS has reasonable correction programs specifically designed for these situations. For TPA recommendations, I'd definitely second the mentions of Ubiquity Retirement and also suggest looking into Guideline or Human Interest - both have solid reputations with small business retirement plans. When you're evaluating TPAs, make sure to ask specifically about: 1. Their experience with S-Corp Solo 401k plans (the contribution calculations are different from sole proprietorships) 2. Whether they include plan document updates and amendments in their annual fee 3. How they handle historical compliance reviews for new clients 4. Their process for Form 5500 filings and what backup documentation they maintain Given that you're 6-7 years from retirement and have substantial assets, I'd also recommend asking any potential TPA about distribution planning strategies. Some TPAs can help coordinate with your tax advisor to optimize your withdrawal strategy when the time comes. The annual cost for full TPA services typically runs $800-1500 depending on your plan complexity, but it's absolutely worth it for the peace of mind and professional oversight, especially as you approach retirement.

Don't forget to think about state taxes too! My boyfriend and I have a similar situation, and while the federal filing was pretty straightforward once we figured out who should claim our daughter, the state rules were different. Some states have their own versions of credits and different rules for unmarried parents.

Great question! I was in a very similar situation a few years ago. One thing that really helped us was creating a detailed spreadsheet of all our household expenses to figure out who was actually contributing more than half for the Head of Household determination. We tracked everything - rent, utilities, groceries, childcare, even things like our son's clothes and medical expenses. It turned out that even though my partner made less money, she was actually covering more of the day-to-day expenses while I was paying the bigger bills like rent. We also discovered that the Child and Dependent Care Credit could be pretty valuable - you can claim up to $3,000 in childcare expenses for one child, and the credit percentage depends on your income level. One mistake we made initially was not coordinating our W4 withholdings properly. Make sure whoever is claiming your son adjusts their W4 to account for the additional credits they'll receive, otherwise you might end up with a huge refund (which is essentially an interest-free loan to the government). The IRS withholding calculator on their website is actually pretty helpful for this once you know who's claiming what.

Has anyone ever been audited for claiming points that were technically paid by the builder? I'm in a similar situation and tempted to just claim them since it seems like such a gray area, but worried about consequences.

I actually went through an IRS audit last year for this exact situation with my Pulte home from 2021. I had claimed about $4,800 in points that were technically paid through a builder incentive program, similar to your situation. The auditor was surprisingly reasonable about it. She explained that what really matters is the economic substance of the transaction, not just who technically wrote the check at closing. In my case, I was able to show that I had negotiated a higher purchase price specifically to get the incentive that covered the points, which meant I was effectively paying for them through my mortgage. The key documentation that saved me was my purchase agreement which showed the original list price, then the "adjusted" price that included the incentive value, and email correspondence with my sales rep discussing how we were using the incentive for rate buydown. The auditor accepted this as evidence that I had constructively paid for the points. That said, she did mention that not all builder incentive situations would qualify - it really depends on how your specific transaction was structured and documented. I'd definitely recommend keeping very detailed records and maybe getting professional advice before claiming the deduction if you're unsure.

Has anyone tried using Credit Karma Tax (now called Cash App Taxes) for previous years? I know they're free for the current year, but I'm not sure if they offer past years or what they charge.

I just went through this exact situation a few months ago! Had to file my 2018 and 2019 returns for a mortgage application. Here's what I learned: For H&R Block, yes they do prior year returns but their online service for old years is around $70-80 per return, which adds up fast. I ended up going with FreeTaxUSA like someone mentioned - it was only $15 for federal and worked perfectly for both years. One tip nobody mentioned: if you're really pressed for time, you can request a "Record of Account" transcript from the IRS online at irs.gov. This shows your filing history and is often accepted as proof of non-filing if you need to show you haven't filed yet. Takes about 5 minutes to get it online versus waiting weeks for mailed returns to process. Also, don't stress too much about the old tax law changes between those years - most tax software handles the year-specific rules automatically. The main thing that changed between 2018-2019 was some small adjustments to tax brackets and standard deduction amounts, but the software calculates all that for you. Good luck getting it sorted out!

I've been dealing with a similar situation with my Altrua HealthShare membership. One thing that helped clarify things for me was understanding that the IRS Publication 502 specifically addresses what qualifies as medical expenses. The key distinction is between what you pay FOR medical care versus what you pay TO SUPPORT a health sharing arrangement. Your monthly shares are considered contributions to support the ministry's operations and other members' needs - not direct payments for your own medical care. However, any medical expenses you pay out-of-pocket (deductibles, copays, services not covered by the sharing ministry) can potentially be deductible if you itemize. This includes things like prescription costs, dental work, or specialist visits that the ministry didn't fully cover. One tip: if your sharing ministry has a "personal responsibility" amount (similar to a deductible), those out-of-pocket payments for your own care would likely qualify as deductible medical expenses, subject to the 7.5% AGI threshold. Keep detailed records separating your monthly ministry contributions from your actual medical expense payments - this will make tax time much easier and help if you face any IRS questions down the road.

Just wanted to add another perspective as someone who's been using Medi-Share for about 5 years now. The tax treatment can definitely be confusing, but I've found it helpful to think of it this way: your monthly shares are like insurance premiums (not deductible), while any medical expenses you pay yourself are potentially deductible. One thing I learned the hard way is to keep separate bank accounts or at least very detailed records. I use one account for my monthly shares to other members, and track all my out-of-pocket medical expenses separately. This makes it much easier at tax time to calculate what might be deductible. Also, don't forget about things like medical travel expenses if you had to go out of town for treatment that your sharing ministry covered. The IRS allows deduction of mileage or actual transportation costs to and from medical appointments, even if the treatment itself was paid for by other members. For what it's worth, I've never had any issues with the IRS regarding my health sharing ministry arrangement, but I always keep very detailed records just in case. The key is being able to clearly separate what you paid to support the ministry versus what you paid for your own medical care.