19 From my experience as a full-time Uber/Lyft driver, the key thing the IRS is looking for is consistency in your record-keeping method. If you create a system and stick with it all year, you're much less likely to be questioned. What I do: I take a photo of my odometer at the start of each shift and another at the end (with timestamps). I keep a super simple spreadsheet with date, starting miles, ending miles, which app I was driving for, and total business miles. That's it. Been doing this for 4 years, never had a problem with the IRS. The people saying you need origin/destination for every trip are probably mixing up the requirements for reimbursement from an employer (which is more detailed) versus self-employed mileage deduction (which is more reasonable).

As a tax professional who works with a lot of gig drivers, I can confirm that your daily starting/ending odometer readings are actually a solid foundation for mileage deduction! The IRS doesn't require trip-by-trip logging for delivery drivers like some people think. Here's what you should definitely keep: 1) Date of work, 2) Starting odometer reading, 3) Ending odometer reading, 4) Total business miles, and 5) Brief description like "Pizza Hut delivery shift." The key is being consistent with whatever method you choose. One thing I'd add to your current system: keep track of your total annual mileage (both business and personal) so you can show the percentage of business use. Also, if you use your car for both jobs on the same day, try to separate those entries if possible - it makes things cleaner if you ever get audited. You're not doing anything wrong! Your method is actually pretty good compared to some drivers I've worked with who have no records at all.

I'm really sorry this happened to you - mortgage servicer negligence with escrow accounts is unfortunately more common than it should be, but that doesn't make it any less infuriating when you're the victim. One thing I'd add to the excellent advice already given: make sure your attorney considers the **contractual breach** angle in addition to the RESPA violations. Your mortgage agreement almost certainly contains specific language requiring them to pay property taxes from your escrow account in a timely manner. Their failure to do this isn't just a regulatory violation - it's a fundamental breach of your contract that directly caused you financial harm. Also, when calculating damages, don't forget about **opportunity costs**. The money you had to scramble to pay for redemption fees, attorney costs, and penalties - that money likely came from savings, retirement accounts, or required you to take on debt. Calculate what that money would have earned if it had remained invested, or what interest you're now paying because you had to use credit to cover their mistake. Your situation is exactly why escrow accounts exist in the first place - to protect homeowners from exactly this scenario. The fact that their system failed so catastrophically (to the point where your home was actually sold at auction!) suggests this wasn't just a simple oversight but potentially systemic negligence in how they manage escrow accounts. Stay strong, and don't let them minimize the severity of what happened here.

I'm really sorry you're going through this - it sounds absolutely devastating to almost lose your home because of your mortgage company's negligence. One thing that might help strengthen your case is getting a professional analysis of your mortgage and escrow account history. I've heard good things about services like https://taxr.ai that can analyze all your mortgage documents and create detailed reports showing exactly where and when errors occurred. Having that kind of documentation could be invaluable for your attorney to demonstrate the pattern of mismanagement. Also, definitely file a complaint with the CFPB as others have mentioned. Mortgage servicers often take these complaints more seriously than direct customer complaints, and it creates an official record of their failure. For settlement amounts, given the severity of what happened (your home was literally sold at auction!), I wouldn't lowball yourself. Consider not just the immediate costs you paid, but the ongoing financial impact of that $750 monthly increase. That's $9,000 per year in additional costs caused entirely by their mistake. Over time, that adds up to significant damages. Document everything - every fee, every sleepless night, any medical costs from stress, time off work to deal with this mess. Their negligence put your most important asset at risk, and that deserves meaningful compensation, not just covering your out-of-pocket costs.

Based on what I've seen in this thread, it sounds like you have several good options to explore for maximizing your vehicle deduction. One thing to keep in mind is timing - if you can purchase before December 31st, 2024, you'd get the 80% bonus depreciation rate instead of the 60% rate for 2025. That could mean an extra $2,600 in first-year deductions on a $13k vehicle with 80% business use. Also consider the vehicle weight factor that Ethan brought up. If you can find a used SUV or truck over 6,000 lbs GVWR in your price range, you might qualify for full Section 179 expensing instead of bonus depreciation, which could be even better than the bonus depreciation route. For documentation, definitely start that mileage log from day one - apps like MileIQ make it pretty painless. The IRS really scrutinizes vehicle deductions, so having solid records is crucial. Have you considered whether you'd actually drive enough business miles to make the standard mileage rate (67 cents/mile for 2024) more beneficial than the actual expense method? At 80% business use, you'd need to drive about 15,500 business miles annually for standard mileage to beat the depreciation approach on a $13k vehicle.

For checking GVWR specs before shopping, I'd recommend using the manufacturer's official spec sheets or the NHTSA vehicle database at nhtsa.gov/vehicle-identification-number. You can also check Edmunds.com or KBB.com which usually list GVWR in their detailed specs section. Some popular used vehicles that typically exceed 6,000 lbs GVWR in your price range include: - Chevy Tahoe/Suburban (like Ethan mentioned) - Ford Expedition - GMC Yukon - Nissan Armada - Most full-size pickup trucks (F-150, Silverado, Ram 1500) Just double-check the specific year and trim level, as base models sometimes fall just under 6,000 lbs while higher trims exceed it. One more timing consideration - if you do find a qualifying vehicle and purchase before year-end, make sure to actually place it in service for business use before December 31st to claim the deduction. Simply buying it isn't enough; you need to start using it for business purposes. Given your high business mileage (18k-20k annually), you're definitely on the right track with actual expenses + depreciation. That's going to save you thousands compared to standard mileage rate.

Has anyone actually calculated whether Roth or Traditional is better for a 1099 contractor? I'm in a similar situation but I'm not convinced Roth is automatically better just because I'm over the deduction limit for traditional contributions. Couldn't I still make non-deductible traditional contributions and benefit from tax-free growth, then strategically convert portions during lower-income years? I'm wondering if the math works out better that way vs paying full taxes now on Roth contributions.

Great thread! I wanted to add that I recently went through this exact same process. After reading through all the helpful suggestions here, I ended up calling Schwab directly using the retirement specialist department approach mentioned earlier. What I learned is that even though Schwab can technically handle Roth SEP contributions now, they require you to specifically request it during account setup - it's not offered as a default option. The rep I spoke with said many customers don't realize this and end up with traditional SEP IRAs when they actually wanted Roth contributions. One thing to keep in mind is that unlike regular Roth IRAs, there are no income limits for Roth SEP contributions. So even high earners can take advantage of this option, which makes it particularly valuable for successful 1099 contractors. I'd definitely recommend calling the retirement specialist departments at the major brokerages rather than going through general customer service. They seem much more knowledgeable about these newer options and can walk you through the specific forms needed.

I'm going through something very similar with our volleyball booster club right now! We also had our 1023-EZ rejected and were told we'd need to file the full 1023 with that hefty fee. Reading through all these responses has been incredibly helpful - I had no idea there were so many resources available. One thing I wanted to add that might help others: our rejection came with a very generic letter that didn't specify the exact issue. After reading the comments here about contacting the IRS directly, I'm definitely going to try using Claimyr to actually get through to someone who can explain what went wrong. The idea of waiting on hold for hours has been keeping me from trying, but if they can get me connected to the right department quickly, that seems worth the cost. I'm also curious about the fiscal sponsorship option that was mentioned - has anyone here actually used that arrangement? It sounds like it might be a good interim solution while we figure out whether to pursue our own 501(c)(3) status or just operate under another organization's umbrella permanently. Thank you everyone for sharing your experiences - it's reassuring to know we're not alone in dealing with this frustrating process!

I completely understand the frustration you're going through - our soccer booster club faced the exact same situation last year! After our 1023-EZ rejection, we were ready to give up entirely, but I'm so glad we didn't. The key insight that saved us was understanding that most 1023-EZ rejections are due to correctable errors rather than actual ineligibility. In our case, we had made two critical mistakes: we included projected fundraising income instead of only actual past receipts, and we hadn't clearly articulated our educational purpose in supporting the school's athletic program. Before spending the $875 on the full 1023, I'd strongly recommend taking advantage of some of the resources mentioned in this thread. We ended up using a combination approach - first, we used Claimyr to get through to an IRS specialist who explained exactly what went wrong with our application. Then we worked with a nonprofit accountant (found through our local SCORE office) to correct the issues and resubmit the 1023-EZ. The whole process took about 3 months, but our corrected 1023-EZ was approved, saving us hundreds of dollars and maintaining our small organization status. The nonprofit designation has been invaluable - not just for tax purposes, but for grant opportunities and donor confidence that we never had before. Don't lose hope! Your booster club serves an important educational purpose, and with the right guidance, you should be able to get this resolved without the full 1023 expense.