This thread has been incredibly helpful! I'm in a similar situation - 100% commission real estate agent driving about 40k miles annually with zero reimbursement from my brokerage. From what I'm reading, it sounds like my classification as a W-2 vs 1099 vs statutory employee is the key factor. My brokerage treats me as an independent contractor (1099), so I should be able to deduct all my business mileage on Schedule C, correct? I've been terrible about tracking though - mostly just estimating based on my annual odometer readings. After seeing the audit story and Google Maps suggestion, I'm definitely going to start using a proper mileage app going forward and try to reconstruct this year's data using my MLS appointments and Google timeline. One question for the group: if I use the standard mileage rate, can I still deduct other car-related expenses like car washes or maintenance specifically for keeping my vehicle presentable for clients? Or is it one or the other?

This is such a valuable discussion! I'm seeing a lot of confusion about employee classification, which is totally understandable given how complex this area can be. One thing I'd add is that if you're unsure about your classification, it's worth requesting a determination from the IRS using Form SS-8. This gives you an official ruling on whether you should be treated as an employee or independent contractor, which can be crucial for cases like this where thousands of dollars in deductions are at stake. Also, for those tracking mileage going forward - don't forget that the business purpose documentation is just as important as the mileage itself. The IRS wants to see WHO you met with, WHERE, and WHY it was business-related. So "Client meeting with Smith family - showing properties on Elm Street" is much better than just "client meeting." Keep excellent records and don't be afraid to push back on your employer if you believe you're misclassified. The tax savings on 30-45k miles could be life-changing!

Anyone know if Cash App's tax documents are usually accurate? Last year I had issues with Robinhood where their 1099 had some incorrect cost basis info and it created a huge headache.

Great question about Cash App's tax document accuracy! I've been using Cash App for trading for about 2 years now and generally find their 1099-B forms to be reliable, but like Diego mentioned, it's always worth double-checking. One thing I learned the hard way - make sure to keep your own records throughout the year rather than relying solely on their year-end documents. I use a simple spreadsheet to track each trade with the date, symbol, shares, buy/sell price, and any fees. This makes it much easier to spot any discrepancies when the 1099-B arrives. Also, if you do find errors on your 1099-B, Cash App's customer support can usually provide corrected forms, but it can take a few weeks during tax season. So the earlier you review your documents, the better! The wash sale tracking seems to be where most platforms struggle, so that's definitely worth paying extra attention to if you've done any frequent trading in the same stocks.

This thread has been incredibly helpful! I'm in a similar situation with a triplex I just purchased. One thing I want to emphasize for fellow newcomers is the importance of getting this allocation right from the start, because it affects your entire depreciation schedule for decades. I made the mistake of initially treating all my closing costs as a single "acquisition expense" without splitting between land and building. My accountant had to help me correct this before filing, and it would have cost me thousands in lost depreciation deductions over the years. For anyone feeling overwhelmed by all this, don't be afraid to invest in professional help upfront. A good tax professional who specializes in real estate can save you way more money in properly structured depreciation than they cost in fees. The rules around what counts as acquisition costs vs. loan costs vs. immediately deductible expenses can be tricky, especially for first-time investors. The 50/50 split approach using tax assessment values is solid, but also consider getting an appraisal if those assessed values seem way off from what you actually paid or current market conditions. Some areas have outdated assessments that don't reflect true land vs. building values.

This has been such a comprehensive discussion! As someone who just bought my first rental property last month, I'm saving this entire thread for reference. One thing I want to add for other newcomers - don't forget about the Section 179 deduction for personal property items that come with your rental. Things like appliances, carpeting, and window treatments can often be deducted in full the first year rather than depreciated over their normal recovery periods. This can provide some immediate tax relief while you're getting used to managing the longer-term building depreciation. Also, I learned the hard way that you need to start thinking about these allocations before you even close. I wish I had asked my realtor or attorney during the purchase process to help me identify which closing costs were which. Going back through the settlement statement weeks later trying to figure out what each line item represents was much more difficult than addressing it in real time. The 50/50 split approach definitely seems like the way to go for most situations. I used my county's online property records to verify that my tax assessment breakdown was reasonable compared to similar recent sales in the area. Having that extra documentation gave me more confidence in my allocation.

I remember this credit! The original 2008 version was basically a $7,500 interest-free loan you had to pay back over 15 years. Lots of people got confused because later versions (2009-2010) turned into a true credit you didn't have to repay if you kept your home long enough. What sucks about your situation is that since you sold the home in 2016, the ENTIRE remaining balance would have become due on your 2016 taxes. That's probably why your 2018 and 2019 returns are getting rejected - there's an outstanding balance the IRS is looking for. The fact that BoA mentioned your loan was from 2009 is probably because of the refinance, which is a separate issue from the homebuyer credit. I suggest calling the IRS (I know, painful) and asking specifically about your Form 5405 from 2008 and what the remaining balance is. Then file your 2016 return with that repayment info.

This is a really complex situation, but it sounds like you definitely received the 2008 First-Time Homebuyer Credit even though you weren't aware of it. The key detail is that September 2008 refund showing up right around your home purchase - that's almost certainly the $7,500 credit. Here's what likely happened: Your tax preparer included Form 5405 on your 2008 return, which triggered the credit. The 2008 version was structured as an interest-free loan requiring $500 annual repayments starting in 2010. The critical issue is that when you sold in 2016, you should have repaid the entire remaining balance (roughly $4,000-4,500) on that year's tax return using Form 5405 Part II. Since you didn't file in 2016, that outstanding balance is now preventing your newer returns from being accepted. Your action plan should be: 1. Get your complete tax transcript for 2008 to confirm the exact credit amount 2. Calculate remaining balance (original amount minus any payments from 2010-2015) 3. File your 2016 return immediately with Form 5405 showing the full repayment 4. Once 2016 is processed, then file your 2018 and 2019 returns The Bank of America loan modification issue is separate - they were likely referring to your 2009 refinance date, not the original mortgage or the tax credit. This is definitely fixable, but you'll need to tackle that missing 2016 return first to clear the IRS block.

Just to add another perspective - I asked my tax accountant about a similar situation with tech stocks (selling Microsoft at a loss and buying Google), and she said it's completely fine. The key is that they're different companies with different business models, revenue streams, etc., even if they're in the same sector. She also mentioned that the IRS has never issued super clear guidance on what exactly "substantially identical" means beyond the obvious cases (like selling and buying back the same stock), so they generally interpret it narrowly.

This is a great question and you're smart to think about the wash sale implications before making the trade. Based on everything I've read and my own experience with tax-loss harvesting, you should be completely fine switching from Barrick Gold to Newmont. The IRS defines "substantially identical" very narrowly - it really only applies to the exact same security or something directly tied to it (like call options on the same stock). Two different companies, even in the same industry with similar business models, are considered distinct securities with their own unique risk profiles, management teams, asset bases, and financial structures. I've done similar sector switches myself - sold some underperforming bank stocks and bought different banks, energy companies for other energy companies, etc. Never had any issues with wash sale disallowances. The key is that GOLD and NEM are completely separate publicly traded companies with different ticker symbols, different management, different mining operations, and different financial performance. Just make sure you're making the investment decision based on your analysis of the companies' fundamentals rather than purely for tax reasons. If you genuinely believe Newmont is a better investment than Barrick going forward, then the tax loss harvesting is just a nice bonus on top of what should be a sound investment decision.