One thing nobody has mentioned yet is that the rules for Roth IRAs were different when Thiel made his initial contributions back in the late 90s. The income limits were higher relative to top earners' incomes, and some of the current restrictions didn't exist. Plus, the IRS wasn't as focused on monitoring these strategies back then. It's kind of like how some tax loopholes get closed after people start exploiting them widely. The super-wealthy are often the first to identify and use these strategies before they become widely known and potentially restricted.

This is such a fascinating example of how timing and access to opportunities can create massive wealth advantages. What strikes me about the Thiel situation is that it wasn't just about knowing the backdoor Roth strategy - it was having access to pre-IPO shares that 99.9% of people could never get. I've been doing backdoor Roth conversions for a few years now (thanks to the income limits), but obviously I'm buying index funds, not PayPal shares at $0.001 each! It really highlights how the same tax-advantaged accounts can have wildly different outcomes based on what investment opportunities you have access to. The self-directed IRA route sounds interesting but also terrifying from a compliance standpoint. Between the prohibited transaction rules, valuation requirements, and increased IRS scrutiny, it seems like something where one small mistake could cost you way more than you'd save in taxes.

Great thread everyone! I'm dealing with something similar and wanted to share what I learned from my tax preparer. For the original question about the $1300 window - you're definitely on the right track with the Energy Efficient Home Improvement Credit. One thing I didn't see mentioned is that you need to make sure the window has the ENERGY STAR label specifically, not just any "energy efficient" window. The contractor saying it "might qualify" suggests you should double-check this. The manufacturer's certification statement should explicitly state it meets the requirements for the federal tax credit. Also, since this credit has been popular, the IRS has been pretty strict about documentation. I'd recommend keeping not just your receipt, but also photos of the ENERGY STAR label on the window itself if possible. Better to have too much documentation than not enough! @Aisha - definitely worth pursuing this credit. Even if it seems like a hassle, $390 back (30% of $1300) is real money. Just make sure you have all the right paperwork before filing.

This is such a helpful thread! I'm going through something similar right now - replaced two windows in my home office last fall and wasn't sure about claiming the credit. After reading through all the advice here, I feel much more confident about moving forward. The key points I'm taking away are: make sure the windows have ENERGY STAR certification (not just "energy efficient"), keep all receipts AND get the manufacturer's certification statement, and use Form 5695 to claim the 30% credit. One question I have - does it matter which room the windows are in? I see the original poster mentioned their living room window, and someone else talked about bedroom windows. I'm assuming it doesn't matter as long as it's your primary residence, but wanted to double-check since mine were in a home office. Also really appreciate the tip about taking photos of the ENERGY STAR labels! Going to do that for the second window I'm planning to replace this spring.

My experience with Dissomaster in my California divorce was that both attorneys and the mediator were confused about tax implications. They initially had me as HOH even though I only had 25% custody because I was claiming one child as dependent. What ultimately worked for us was getting a tax professional involved who specializes in divorce situations. She pointed out that the Dissomaster calculations would be significantly off if they used incorrect filing status. When corrected to Single (while still claiming one dependent), my support obligation was adjusted by almost $400/month! Make sure you address this before finalizing anything. The tax filing status makes a huge difference in the support calculations, and many mediators don't fully understand the difference between dependency exemptions and filing status requirements.

I've been a family law paralegal for 8 years, and I see this mistake ALL THE TIME. The tax filing status in Dissomaster has a significant impact on the final numbers. For California specifically, the court is supposed to use the tax filing status that each parent is "entitled to use" under federal law. If you only have 20% custody, you are NOT entitled to use Head of Household - period. Even if you're claiming a child as a dependent by agreement. Print out the IRS rules for HOH qualification (specifically the residency test requirement) and bring it to your next mediation. The mediator should correct your filing status to Single while still allowing you to claim one child as a dependent per your agreement.

Has anyone used TurboTax to report a home sale? I'm selling my house next month and wondering how complicated the forms are for reporting it.

Just to add another perspective - I'm a tax preparer and see this confusion a lot during tax season. The Section 121 exclusion is one of the most misunderstood parts of the tax code because people mix it up with 1031 exchanges or remember old rules from decades ago. Rita, you're absolutely fine to take your time finding the right property. The $250k exclusion ($500k for married filing jointly) applies regardless of whether you buy another home, when you buy it, or even if you never buy again. The only requirements are that you owned and used the home as your primary residence for at least 2 of the 5 years before the sale, which you clearly meet. One small thing to keep in mind - if you do eventually buy and sell another primary residence, you can use this exclusion again, but generally not more than once every 2 years. Since you're taking time to find the right place, this timing rule shouldn't be an issue for you. Your financial advisor gave you the correct information. Enjoy living with your parents while you take your time finding the perfect next home!

The discussion here is super helpful but there's one thing I haven't seen addressed: rental income. I have a similar situation (W2 plus consulting plus software sales), but I also own a couple rental properties. Does rental income qualify for QBI? Some accountants told me yes, others said no.

This is exactly the kind of complex QBI situation that trips up so many people! Diego, based on your income breakdown, you're definitely going to want to be strategic about this. Your W-2 income of $135k doesn't qualify for QBI at all - that's correct. For your self-employment income ($65k consulting + $70k software = $135k total), you're looking at potential QBI on that $135k, but with important caveats. The key issue is that your total income of $270k likely puts you above the phase-out thresholds ($170,050 single/$340,100 MFJ for 2023). This means your engineering consulting income will be significantly limited or eliminated from QBI since it's an SSTB. However, your software sales income might still qualify if it's truly product-based rather than service-based. The distinction others mentioned about custom vs. packaged software is crucial here. One strategy to consider: maximizing retirement contributions (SEP-IRA, Solo 401k) to potentially get your taxable income below the phase-out thresholds. Even a partial reduction could save you thousands. Also, make sure your CPA considers the W-2 wage limitation that applies at higher income levels - this could further complicate your QBI calculation even for the qualifying income streams. The tools others mentioned (taxr.ai, claimyr.com) seem worth exploring for the analysis, but definitely still work with your CPA for the final filing!