Slightly off topic but does anyone know if section 179 vehicles have to be over 6000 lbs? Im looking at buying a work vehicle but I'm not sure if my SUV qualifies.

I'd strongly recommend consulting with a tax professional before making any moves here. The recapture rules for Section 179 are pretty strict - when you sell that truck, you'll likely owe ordinary income tax on the sale proceeds up to the amount you originally deducted ($98k). One thing to consider is the timing of both transactions. If you're planning to buy another qualifying vehicle this year, you might want to structure the timing so that the recapture income from the sale is partially offset by the new Section 179 deduction. This won't eliminate the tax hit entirely, but it could help manage the cash flow impact. Also keep in mind that there are annual limits on Section 179 deductions ($1,160,000 for 2023), so make sure you have enough "room" left if you've already taken other business deductions this year. The rules can get complex when you're dealing with multiple transactions in the same tax year.

Just wanted to add some perspective as someone who went through this exact situation a few years ago. The good news is yes, you can absolutely max out both your SIMPLE IRA and Roth IRA - they're completely separate contribution buckets. One thing I wish someone had told me earlier: don't forget about the timing of your contributions! While you have until the tax deadline to contribute to your Roth IRA, your SIMPLE IRA contributions need to come out of payroll during the actual tax year. So if you want to max out your SIMPLE IRA for 2025, you need to adjust your payroll deductions now to spread that $15,500 across your remaining paychecks. Also, since you mentioned feeling behind on retirement savings at 43, you might want to start planning for catch-up contributions. Once you hit 50, you can contribute an additional $3,500 to your SIMPLE IRA and $1,000 to your Roth IRA. That's an extra $4,500 per year you can sock away! The dual employer/employee role can be confusing, but it's actually an advantage - you get to contribute as an employee AND give yourself the employer match. Just make sure you're giving all your employees the same match percentage you give yourself.

Great question! I'm actually a CPA who works with a lot of small business owners in similar situations. The short answer is YES - you can absolutely max out both your SIMPLE IRA ($15,500 for 2025) and your Roth IRA ($7,000 for 2025) as long as you meet the income requirements for the Roth. The key thing to understand is that these are completely separate contribution limits. Your SIMPLE IRA is an employer-sponsored plan, while your Roth IRA is an individual retirement account. Being the business owner doesn't change your ability to contribute to both - you're still treated as an employee for SIMPLE IRA purposes. A few important points to keep in mind: - Make sure your income falls within the Roth IRA phase-out limits ($146,000-$161,000 for single filers in 2025) - Don't forget you also need to provide yourself the same 3% employer match you give your employees - At 43, you're actually not that far behind - you still have 22+ years until full retirement age to build your savings Since you mentioned feeling behind on retirement savings, maxing out both accounts would put away $22,500 this year (plus your employer match), which is a solid foundation to build on. You're asking the right questions and taking the right steps!

I work in IT for a tax preparation firm and want to add some technical context about .T19 files that might help others understand their options better. These files use a proprietary compression format that's deliberately designed to be difficult to open without H&R Block's software - it's part of their customer retention strategy. However, if you're tech-savvy and just need to extract basic information (not a pretty formatted return), you can sometimes get partial success by treating the .T19 file as a ZIP archive and extracting the XML data inside, as someone mentioned earlier. The XML won't be human-readable without understanding H&R Block's field codes, but you might be able to pull out key numbers like AGI, total tax, etc. with some patience. That said, for mortgage applications, I'd strongly second the recommendations to go with official IRS transcripts instead. They're free, immediately available, legally recognized, and lenders actually prefer them because they can't be manipulated. The Get Transcript service really is your best bet - don't overcomplicate this with file conversion attempts when the IRS has already solved the problem for you.

I just wanted to share my experience as someone who went through this exact same frustration last year. After trying several of the solutions mentioned here, I found that the combination approach really works best. First, definitely start with searching your email - I found two years of returns in my Gmail by searching for "tax return filetype:pdf" which pulled up the H&R Block confirmation emails with PDF attachments. For the missing years, the IRS Get Transcript service was a lifesaver once I got through the identity verification. One thing I'd add that hasn't been mentioned: if you're doing this for a mortgage, ask your lender if they accept "Wage and Income Transcripts" in addition to the full "Tax Return Transcripts." The wage and income version downloads faster and contains the key information most lenders need (W-2s, 1099s, etc.). My broker said either format worked fine for their underwriting requirements. The whole process ended up being way less complicated than I initially thought. Don't let the .T19 file format stress you out - there are definitely free solutions that will get you what you need without paying H&R Block again!

Just wanted to add something that might help folks who are dealing with this situation - if you're feeling overwhelmed by the paperwork and deadlines, consider tackling this in phases rather than trying to do everything at once. I went through something similar last year and found it much more manageable when I broke it down like this: Phase 1 was just identifying which years I needed to deal with and requesting all the IRS transcripts. Phase 2 was organizing the documents and doing rough calculations to prioritize which years to file first. Phase 3 was actually preparing and filing the returns one year at a time. This approach helped me avoid the paralysis that comes from looking at a huge pile of unfiled tax years all at once. Plus, if you run into any complications or questions with the first return you file, you can address those issues before tackling the remaining years. Also, don't beat yourself up about letting this slide for so long - life happens and tax obligations can easily fall through the cracks when you're dealing with multiple jobs, school, moving, or other major life changes. The important thing is that you're addressing it now while you can still claim those refunds. Better late than never!

I just wanted to chime in as someone who recently went through this exact process! Found old W-2s from 2019-2022 and was able to successfully claim refunds for three of those years. One thing I'd add that hasn't been mentioned yet - if you're missing any documentation and your former employers are no longer in business or unresponsive, don't panic. The IRS wage transcripts that others have mentioned are incredibly thorough. I was missing W-2s from two companies that had closed down, but the transcripts showed all the income and withholding information I needed to complete those returns. Also, @Edison Estevez, since you mentioned being "all over the place" with jobs during that period - I was in a similar situation with gig work, part-time jobs, and even some under-the-table work I wasn't sure how to handle. The key is just to report what you have documentation for. Don't stress about income that was never reported to the IRS if you don't have records of it. The whole process took me about 3 months from start to finish, but seeing those refund deposits was absolutely worth the effort. I ended up getting back about $2,800 across the three eligible years. Sometimes procrastination pays off in unexpected ways when you finally get around to fixing it!

This is a really thoughtful question that highlights how complex the EV tax credit can be with different filing statuses! Based on what you've described, your wife would likely qualify for the full $7500 credit if you file separately, since her individual AGI is under the $150k threshold. However, before making this decision, I'd strongly recommend calculating the medical expense deduction benefit first. Medical expenses are only deductible when they exceed 7.5% of AGI - so if your wife's AGI is around $140k, she'd need over $10,500 in medical bills to see any deduction benefit. If the medical expenses don't clear this threshold on her individual income, you might be giving up joint filing benefits unnecessarily. A few key requirements if you proceed: - The EV must be purchased and titled solely in your wife's name - She needs at least $7500 in federal tax liability to use the full credit - Verify the specific vehicle model qualifies for the full amount - Consider the point-of-sale discount option to get the benefit immediately Don't forget that filing separately often means losing other valuable benefits like certain education credits, IRA deductibility, and student loan interest deductions. The $7500 EV credit is substantial, but make sure you run comprehensive projections both ways to see the total impact. Given the dollar amounts involved and the complexity of coordinating the medical expenses, EV credit, and various other tax implications, this might be a great case for consulting with a tax professional who can model both scenarios with your actual numbers. Good luck with the decision!

This is such a comprehensive discussion with excellent advice from everyone! I wanted to add one more perspective that might be helpful for your decision-making process. Since you're dealing with both the medical expense deduction and EV credit considerations, timing could work in your favor here. You mentioned the medical bills are from this year, but you're also considering an EV purchase before year-end. This gives you a unique opportunity to optimize both benefits in the same tax year. Here's what I'd suggest: First, calculate exactly what your wife's medical expense deduction would be on her individual AGI (remember, only the amount over 7.5% of AGI is deductible). If that deduction is substantial, then filing separately already makes sense even without the EV credit. The EV credit would just be additional savings on top. However, if the medical expenses barely clear the 7.5% threshold or don't provide much deduction benefit, you might want to reconsider the separate filing strategy entirely. One practical tip: Many people don't realize that you can actually prepare your taxes both ways (joint and separate) before filing to see which gives you the better outcome. Most tax software will let you run both scenarios. This could help you see the complete picture including the EV credit, medical deductions, and all other impacts before making your final decision. Also, since you're considering this decision "soon before year-end," make sure you factor in any state EV incentives that might stack with the federal credit - these can sometimes have different timing requirements or eligibility criteria that could influence when you want to make the purchase. Hope this helps with your planning!