This is such valuable information! As someone who just started with Uber Eats last month, I had no idea about the self-employment tax kicking in at just $400. I've been assuming I'd be fine since I'm nowhere near the regular filing threshold. Quick question for the group - when you say "set aside 25-30%" for taxes, is that from gross earnings or after deducting expenses like mileage? I've been tracking my miles but wasn't sure if I should calculate my tax savings based on total earnings or what's left after the mileage deduction. Also, does anyone know if there's a grace period for first-time 1099 filers? Like, will the IRS be more lenient with penalties if you legitimately didn't know about the self-employment tax requirement?

Just wanted to add something that might help other newcomers like myself - the IRS also has a "First Time Penalty Abatement" (FTA) policy that can waive failure-to-file and failure-to-pay penalties for taxpayers who have been compliant in prior years OR have no prior filing history. Since you mentioned you've never filed before, you might qualify for this if you end up with penalties. You'd need to call the IRS (or use that Claimyr service others mentioned) to request it after you file your return. Also, don't forget that as a delivery driver, you can deduct more than just mileage - things like your phone data plan percentage used for work, insulated delivery bags, car maintenance related to delivery work, and even parking fees during deliveries can add up to significant savings. The key is keeping good records from the start. I wish someone had told me this when I began - it would have saved me a lot of stress and money!

This is such a frustrating situation, and I feel for you dealing with this mess. I wanted to add one more potential avenue that hasn't been mentioned yet - consider reaching out to your state's insurance commissioner's office as well. Since Lincoln Financial is an insurance company operating in your state, they're regulated not just by FINRA but also by your state insurance department. Many state insurance commissioners have consumer protection divisions that can put additional pressure on companies to resolve situations like this. I'd also recommend documenting the timeline very carefully - specifically when you first contacted the advisor, when they made their recommendations, and when the actual transfers occurred. If there's evidence that they marketed themselves as retirement planning experts or inherited IRA specialists, that strengthens your case significantly. One thing that struck me from your post is that you mentioned the advisor "mainly push insurance products for commissions." This suggests they may not have been properly qualified to give advice about inherited IRAs in the first place. Make sure to include this context when you file complaints - it shows they were operating outside their area of expertise. The fact that multiple people here have had success with IRS relief procedures gives me hope for your situation. The key seems to be thoroughly documenting that you relied on professional advice and would never have made this transfer without their explicit recommendation. Keep fighting this - $30K is way too much to lose due to someone else's professional negligence.

I'm really sorry to hear about this situation - it's exactly the kind of inherited IRA mistake that can be financially devastating. Based on everything shared in this thread, you definitely have multiple paths forward and shouldn't give up. One thing I'd add to all the excellent advice already given: make sure you're working with a tax professional who specifically has experience with inherited retirement account issues. Not all CPAs or tax preparers are familiar with the nuances of inherited IRA rules and the various relief provisions available. Also, when you're documenting everything for your various complaints and relief requests, focus heavily on the fact that you explicitly sought professional guidance specifically because you wanted to avoid making mistakes with inherited accounts. This demonstrates that you acted reasonably and in good faith - you didn't try to handle complex retirement account transfers on your own, you hired a professional specifically to avoid errors. The combination of IRS relief procedures (Revenue Procedure 2020-46), FINRA complaints, potential E&O insurance claims, and state insurance commissioner involvement gives you multiple shots at recovering most of this money. Even if each avenue only partially succeeds, the combined effect could significantly reduce your financial exposure. Document every phone call going forward, save every email, and don't let Lincoln Financial or the advisor minimize this as a "simple misunderstanding." This was a fundamental error in retirement account handling that any financial professional should have known to avoid.

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.

I'm confused by all of this tbh. Last year I got a $120 settlement check with no 1099 at all, and the year before I got one with a 1099 that had nothing written on it about taxes. Why is there no consistency??

The inconsistency you're seeing is actually pretty normal with class action settlements. Each settlement administrator and their legal counsel make independent decisions about tax reporting based on the specific nature of that settlement. Some factors that affect whether you get a 1099: - Settlement amount (many don't issue 1099s under $600) - Type of damages being compensated - How cautious the administrator wants to be - Whether the settlement clearly falls into taxable vs non-taxable categories Your $120 settlement without a 1099 was probably either under their reporting threshold or clearly determined to be non-taxable from the start. The one with the blank 1099 sounds like they were being extra cautious but didn't have specific tax guidance to include. Bottom line: if you don't get a 1099, you generally don't need to report it. If you do get one with a note saying it's not taxable, keep the documentation and follow their guidance. The settlement administrators usually have tax attorneys making these determinations, so their guidance is typically reliable.

I think everybody is overthinking this. If you have a rental property that isn't a triple-net lease, most tax pros consider it a business eligible for QBI. The 250-hour safe harbor just gives you automatic qualification and protection from challenges. I've been claiming QBI on my 3 rentals for years with no issues. I have property managers for all of them and probably spend less than 50 hours total on them each year. Unless you're blatantly ignoring all aspects of the property, you're probably fine.

I've been through this exact same situation and ended up working with a tax professional who specializes in QBI deductions. What I learned is that the key isn't just how many hours you spend, but the nature and regularity of your activities. In your case, regularly communicating with the PM about maintenance, HOA compliance, inspection scheduling, and tenant renewals actually demonstrates significant business involvement. The fact that you're making decisions and staying involved rather than just collecting rent checks is important. My CPA explained that courts have looked at factors like: Do you maintain separate business records? Do you actively market the property? Do you make business decisions about repairs, improvements, and tenant selection? Are you involved in setting rent rates? Even with a property manager handling day-to-day operations, if you can show you're actively managing the business aspects of the rental, you may have a solid case. The $2,600 in potential tax savings definitely justifies getting a professional opinion from someone who really knows QBI rules. I'd recommend finding a CPA who has experience with rental property QBI cases specifically - it made all the difference for me.