Something nobody mentioned: these billionaires sometimes intentionally take salaries of $1 for PR purposes, claiming they're not taking compensation, while using the loan strategy behind the scenes. It's basically a marketing tactic to appear selfless while actually using more tax-efficient methods.

There's also another strategy that works alongside "buy, borrow, die" - charitable remainder trusts. Billionaires will donate appreciated stock to a trust, get an immediate tax deduction, and then the trust sells the stock without paying capital gains taxes. They can then receive payments from the trust for life while appearing philanthropic. The kicker is they often retain some control over how the money is invested within the trust, and their family members sometimes end up running the charitable foundation that eventually receives the remainder. So they get tax benefits, maintain influence over the assets, and create a legacy vehicle for their heirs - all while reducing their taxable estate. It's another layer of the wealth preservation puzzle that works especially well when combined with the borrowing strategies everyone's been discussing.

Just wanted to add one more important consideration that might help with your decision-making process. Even if you could track down all your contribution records and calculate an exact loss, remember that Roth IRAs are designed for long-term retirement savings - typically 20-40+ years of potential growth. The tax-free compounding over decades is incredibly valuable. For example, if you have $15,000 currently in your Roth accounts that grows at an average 7% annually, that becomes about $225,000 in 40 years - all tax-free. Compare that to whatever deduction you might get (when it becomes available again in 2026) which would likely save you maybe a few hundred to a couple thousand dollars in taxes. The math almost never works out in favor of closing the accounts unless you have truly massive losses AND you're in a very high tax bracket. Most financial advisors would tell you to ride out the temporary losses and focus on your long-term retirement strategy instead. If you're concerned about your current investment performance, consider rebalancing within your existing Roth accounts or adjusting your asset allocation rather than closing everything.

This whole thread has been incredibly educational! As someone who's been contributing to a Roth IRA for about 5 years but never really understood the loss deduction rules, I had no idea it was this complicated. The key takeaway for me is that between the current suspension of miscellaneous itemized deductions through 2025, the requirement to close ALL Roth accounts, and the lost opportunity for decades of tax-free growth, claiming Roth IRA losses is almost never worth it for regular investors like us. I'm curious though - are there any specific scenarios where this might actually make sense? Like if someone had contributed $50,000+ over many years and their accounts were now worth only $10,000 due to really bad investment choices? Even then, giving up that Roth space forever seems like it would hurt more in the long run. Also, for anyone dealing with scattered records across multiple brokerages like the OP, it sounds like the first step should always be contacting your current providers to see what historical data they have before even considering any drastic moves.

One thing I'd add to all the great advice here - make sure you're also considering the timing of your purchase for maximum tax benefit. Since you bought the Tesla in 2025, you can take the Section 179 deduction this year, but if your 1099 income varies year to year, you might want to think strategically about when to claim the deduction. For example, if you expect your business income to be higher next year, you could elect to take less than the full allowable deduction this year and save more for when you have higher business income to offset. The Section 179 election is flexible - you don't have to take the maximum amount available. Also, don't forget about the potential for bonus depreciation on top of Section 179. For 2025, you might be able to combine both depending on your situation. Definitely worth having a tax professional run the numbers to see which depreciation strategy gives you the best overall tax outcome given your specific income mix. Keep those mileage logs detailed and contemporaneous - that's going to be your lifeline if you ever get questioned on the 90% business use!

This is such a helpful thread! I'm in a similar situation with dual income sources and just bought a vehicle for my consulting business. One thing I wanted to add that I learned from my CPA - make sure you understand the difference between the Section 179 deduction and regular depreciation when it comes to recapture if you ever sell the vehicle. With Section 179, if you sell the Tesla before holding it for the full depreciation period, you might have to "recapture" some of that deduction as ordinary income rather than capital gains. This is especially important since you're using it 90% for business. If your business use percentage drops significantly in future years (say you change jobs or your 1099 work decreases), you could face some unexpected tax consequences. Also, @Ava Kim, since you're making good money on both the W-2 and 1099 side, you might want to consider whether taking the full Section 179 deduction in one year is actually optimal from a tax bracket perspective. Sometimes spreading the depreciation over several years can keep you in lower tax brackets and result in better overall tax savings. Just something to discuss with a tax professional who can model out different scenarios for your specific situation!

Has anyone here actually been audited for cash income? What did they specifically ask for? I'm a bartender and get a lot of cash tips that I report honestly, but I don't have any real "proof" besides my bank deposits.

For cash income documentation during an audit, the IRS typically accepts what they call "contemporaneous records" - meaning records made at or near the time of the transaction. Your notebook approach is actually on the right track, but you'll want to enhance it. Key documents that strengthen your case: 1) Daily cash receipts log (your notebook counts, but make entries consistent and detailed), 2) Bank deposit records that correlate with your logged income, 3) Any receipts or invoices you provide to customers, 4) Photos of completed work or service agreements, and 5) Calendar or appointment book showing scheduled jobs. The IRS understands that cash businesses often have less formal documentation, but they look for consistency between your reported income, lifestyle, bank deposits, and spending patterns. Your bank statements showing regular deposits that match your notebook entries will be very helpful. Consider also taking photos of completed work and keeping simple service agreements or at least text messages with clients about job details - these all help corroborate your income claims. The key is showing a reasonable, consistent system rather than perfect documentation.

This AGI mismatch issue is driving me crazy too! I've been dealing with the same rejection for over a week now. What's really frustrating is that I triple-checked my 2023 AGI from line 11 and it's definitely correct. I even pulled up my PDF copy and compared it character by character. I'm seeing a lot of people mention trying $0 as the prior year AGI - that seems counterintuitive but if it works, I'll definitely give it a shot. Has anyone figured out WHY this is happening so much this year? Like is it a system-wide IRS glitch or something with TurboTax specifically? I'm also curious about those transcript services people are mentioning. Might be worth it just to see what the IRS actually has on file vs what I think they should have. This whole situation is making me want to switch tax software next year honestly.

This AGI mismatch rejection is such a widespread issue this filing season! I went through this exact same frustration a few weeks ago. After trying everything - double-checking my 2023 AGI multiple times, creating an IRS online account, even calling their helpline (total waste of time) - what finally worked was the $0 trick that several people mentioned here. I know it sounds completely backwards to enter $0 when you KNOW your AGI is correct, but apparently the IRS systems are expecting this if they made any backend adjustments to your 2023 return that you weren't notified about. It's like their left hand doesn't know what their right hand is doing. If the $0 doesn't work, I'd definitely recommend checking out those transcript analysis tools people mentioned or using a service to actually get through to an IRS agent. Sometimes there are weird system glitches that only they can see and fix on their end. Don't let TurboTax drive you crazy - this isn't your fault and it's definitely fixable! The IRS e-file system has been a hot mess this year but your refund will come through once you get past this hurdle.