Has anyone used the attribution rules to their advantage with family members? I'm thinking about giving my spouse ownership in one of my LLCs to potentially optimize our retirement contributions, but I'm not sure if that would trigger control group issues.

I've been following this discussion closely as someone who recently went through a similar multi-LLC Solo 401k setup. One thing I'd add is the importance of maintaining separate books and records for each entity, even if they end up not being a control group. The IRS will scrutinize whether your businesses are truly separate operations during an audit. Also, make sure you're tracking compensation from each entity separately. Even if the businesses aren't a control group, you can only contribute to a Solo 401k based on the earned income from that specific business. I made the mistake of trying to use combined income across entities and had to correct it later. The documentation from services like taxr.ai that others mentioned becomes really valuable here because it shows you considered all the rules properly. I keep mine with my tax records as backup documentation.

Don't forget about free resources! IRS Publication 17 (Your Federal Income Tax) is comprehensive and updated yearly. For investing, the Bogleheads wiki has excellent articles on tax-efficient fund placement. The book "The White Coat Investor" by James Dahle is aimed at doctors but has universally applicable tax strategies for high earners.

Great thread! I've been diving deep into tax education myself over the past year. One resource that really helped bridge the gap between reading books and practical application was "The Tax and Legal Playbook" by Mark Kohler. What I love about Kohler's approach is that he explains not just WHAT the strategies are, but WHY they work legally and HOW to implement them step by step. He covers everything from basic deductions to more advanced strategies like setting up LLCs for tax benefits. I'd also recommend supplementing whatever books you choose with the IRS's own educational materials - specifically their "Tax Benefits for Education" and "Retirement Plans" publications if you're looking at those areas. They're dry but authoritative. One thing I learned the hard way: start with ONE book, implement what you learn for a tax year, then move to more advanced strategies. I made the mistake of trying to absorb everything at once and ended up more confused than when I started! The combination of Wheelwright's "Tax-Free Wealth" for philosophy and Kohler's book for practical steps has been really powerful for me.

I understand the anxiety you're feeling - I went through something very similar a couple years ago when I couldn't make my final payment due to unexpected car repairs. The stress was overwhelming, but it worked out much better than I expected. Here's what actually happened in my case: I called the IRS about 3 weeks before my deadline and explained my situation. The representative was surprisingly understanding and offered me a few options right on the phone. I ended up extending my payment plan by 4 months with just a $89 fee since I applied for the modification online afterward. The key things that helped my case were: 1) I had made every single monthly payment on time up until that point, 2) I was honest about the unexpected expense, and 3) I called BEFORE missing the deadline rather than after. One tip I wish someone had told me - when you call, ask specifically if you qualify for a "streamlined modification" since you've been compliant with payments. This is faster than a full financial review and often has lower fees. The penalties and interest do continue accruing, but at least for me, the peace of mind of having an approved extension was worth it. And honestly, the IRS representative I spoke with said they much prefer working with people who communicate proactively rather than just disappearing when they can't pay. You've got this - the fact that you're thinking ahead and asking for advice shows you're handling this responsibly!

I've been helping people with IRS payment plan issues for years, and the most important thing to remember is that you have rights and options when you can't meet your deadline. Since you've been making consistent payments, you're already in a strong position. Here's my step-by-step recommendation: 1. **Call immediately** - Don't wait until November. Call the IRS practitioner priority line at 1-866-860-4259 (even as an individual, you can sometimes get through faster here) or the main line at 1-800-829-1040. Call early morning (7-8 AM) for shorter wait times. 2. **Ask for a "payment plan modification"** - Specifically mention that you've been compliant with all payments and need to extend due to medical hardship. Have your payment plan agreement number ready. 3. **Document everything** - Keep records of medical bills and any correspondence with the IRS. If they approve a modification over the phone, ask for written confirmation. 4. **Consider partial payment** - If you can pay anything toward the $3,800 by November (even $500-1000), it shows good faith and may help with the modification approval. The penalties you mentioned are real but manageable - about 0.5% per month plus current interest rates. This is much better than defaulting and facing potential liens or levies down the road. One last tip: if you have trouble getting through by phone, you can also submit Form 9465 (Installment Agreement Request) to formally request the modification. The IRS typically responds within 30 days. You're handling this responsibly by planning ahead. Medical expenses are considered legitimate hardship, so be honest about your situation - they work with people in similar circumstances all the time.

Do I have to do anything special with 199A dividends when using FreeTaxUSA instead of TurboTax? My 1099-DIV has about $32 in box 5 for Section 199A dividends.

Just wanted to add some clarity about the thresholds for Form 8995 vs 8995-A. If your taxable income is under $182,050 (single) or $364,100 (married filing jointly) for 2023, you can use the simplified Form 8995, which is much easier. Above those thresholds, you need the more complex 8995-A. For small amounts like yours ($5.45), you're definitely in simplified territory regardless of your income level. Most tax software like TurboTax will automatically determine which form applies to your situation and handle the calculations behind the scenes. The key is just making sure you enter that Box 5 amount from your 1099-DIV correctly when prompted. One thing to watch out for - if you have multiple 1099-DIVs with 199A dividends, make sure you add them all up. The 20% deduction applies to the total amount across all your qualified sources.

Has anybody used any specific brokerage that makes this stock transfer process easier? I'm with Fidelity and wondering if there's paperwork I need to fill out or if I can do it all online.

One thing to keep in mind that hasn't been mentioned yet - make sure you document everything properly for your records. When you gift stock, you'll want to keep records of the fair market value on the date of transfer (you can use the average of high and low prices for that day), along with your original purchase information. Also, if you're gifting shares worth close to the $19,000 limit, consider doing it earlier in the year rather than waiting until December. Stock prices can be volatile, and you don't want to accidentally exceed the annual exclusion if the stock appreciates between when you plan the gift and when you actually execute it. Your parents should also understand that they'll need this cost basis information when they eventually sell, so make sure to provide them with all the original purchase details - dates, prices, and any relevant documentation.