This thread has been incredibly thorough and helpful! I'm also considering transferring my personal vehicle to my S-Corp and appreciate seeing all the different approaches and real-world experiences shared here. One additional consideration I wanted to mention - make sure to think about how this affects your personal transportation situation if something happens to the vehicle. Since the business will own it, you can't just go out and replace it with personal funds if it breaks down or gets totaled. Your business needs to have a plan (and budget) for repairs or replacement, which might mean keeping more cash reserves than you otherwise would. Also, I've been researching the state tax implications that @ac1b2919e0aa mentioned, and it varies significantly by state. Some states treat this as a taxable sale requiring sales tax, while others have exemptions for transfers to entities you own. In my state (California), there's actually a specific form you can file to avoid paying sales tax on transfers to your own business entity, but you have to file it within a certain timeframe. For anyone considering this strategy, I'd recommend running the numbers on both the standard mileage deduction versus actual expenses before making the transfer. With the current standard mileage rate being pretty generous, the actual expense method only makes sense if your vehicle-related costs (including depreciation) significantly exceed what you'd get with the per-mile deduction. The consensus seems to be that proper documentation is absolutely critical, so I'm planning to consult with both my CPA and attorney before proceeding to make sure I have everything structured correctly from the start.

This has been an absolutely fantastic thread with so much practical advice! As someone who's been on the fence about transferring my personal vehicle to my S-Corp, reading through all these real experiences has been incredibly valuable. I wanted to add one consideration that I learned about recently - the impact on your business's financial statements. When you sell your personal vehicle to your S-Corp, it shows up as both an asset (the vehicle) and a liability (the loan owed back to you) on your business balance sheet. This can affect certain business metrics if you ever need to apply for additional business credit or if you're considering bringing in investors down the road. Also, for those worried about the IRS questioning this arrangement - my CPA mentioned that as long as you're treating it as a legitimate business transaction (fair market value, proper documentation, reasonable interest rate, actual business use), it's a completely acceptable tax strategy. The problems arise when people try to inflate values or don't maintain proper records. One practical tip: I ended up creating a simple spreadsheet to track all the moving pieces - monthly loan payments, business vs personal mileage, maintenance expenses, insurance costs, etc. Having everything in one place makes it much easier when tax season comes around and helps ensure you're capturing all the deductible expenses you're entitled to. Thanks to everyone who shared their experiences - this thread should be required reading for any S-Corp owner considering this strategy!

One thing none of these comments mentioned - the SALT cap is scheduled to expire after 2025! So if you're buying a home now, in just a couple years the cap might go away and you could potentially deduct your full SALT amount again. Of course, Congress could extend the cap or create a new limit, but it's worth keeping in mind for long-term planning.

Great discussion everyone! As someone who went through this exact analysis last year, I wanted to add a few practical tips for @cc288379ec13: 1. Don't forget about PMI - if you're putting less than 20% down, your mortgage insurance premiums are also deductible (subject to income limits). This can add another $1-3k to your itemized deductions. 2. Track your charitable contributions more carefully once you're itemizing. Even small donations to Goodwill, church offerings, etc. can add up to meaningful deductions. 3. Consider timing some deductions strategically. For example, if you're close to the itemizing threshold, you might want to bunch charitable contributions into alternating years to maximize the benefit. The $18k property tax you mentioned is indeed high, but if you're in a state like NY, NJ, or CA, that's unfortunately pretty normal for decent areas. Just make sure you factor in the tax benefits when comparing the total cost of homeownership vs. renting. One last thing - property taxes can increase over time, but your deduction will still be capped at $10k, so factor that into your long-term planning.

Has anyone tried the "import transactions" feature in the desktop version of TurboTax Premier? I heard it might handle wash sales better than the online version, but I don't want to pay for it if it doesn't actually work.

I went through this exact same headache with TurboTax last year and ended up having to manually adjust about 50+ wash sale transactions. The key thing I learned is that you absolutely need to verify each transaction because TurboTax's automatic import often gets the wash sale adjustments wrong. What worked for me was printing out my detailed brokerage statements and going line by line to compare against what TurboTax imported. I found that the software was calculating wash sales incorrectly in cases where I had multiple purchases and sales of the same stock within the 61-day window. One tip that saved me time: focus on the transactions with the largest dollar amounts first. I found several cases where TurboTax had completely missed wash sales on my biggest trades, which would have been a red flag to the IRS. The smaller discrepancies like your $270 vs $13 example are annoying but less likely to trigger problems. It's tedious work but worth doing correctly. The IRS does match your reported numbers against what your broker sends them, and wash sale reporting errors are one of the most common reasons for tax notices.

One thing I'd add to all this great advice - make sure your parents coordinate the timing of the gift with your mortgage application process. Some lenders want to see the gift funds "seasoned" in your account for a certain period (usually 60 days) before closing, while others are fine with recent transfers as long as you have proper documentation. Also, if your parents are married and filing jointly, they might want to consider which parent's name the funds come from for tracking purposes on Form 709. It doesn't change the tax implications, but it can make the paperwork cleaner if they're consistent about how they handle large gifts in the future. Good luck with the house purchase! Getting family help for a down payment is such a blessing in today's market.

Just wanted to add one more practical tip from my experience - make sure to keep copies of everything! When my parents gifted me money for my house, I created a folder with copies of the gift letter, bank transfer records, their Form 709s, and even screenshots of the IRS annual exclusion amounts for that year. This documentation became super helpful not just for the mortgage process, but also when I was doing my own taxes the following year. My tax software kept asking about large deposits, and having everything organized made it easy to show it was a documented gift. Plus, if you ever get audited down the road (unlikely, but still), you'll have a complete paper trail showing everything was done properly. The house buying process is stressful enough without worrying about tax compliance - sounds like you're being smart by researching this ahead of time!

Just wanted to add my experience from handling my uncle's estate last year. We had a very similar situation - house worth about $400k at death, sold for $398k, with $24k in selling expenses. The key thing I learned is that you need to be very careful about how you report this on the 1041. Even though mathematically it looks like a $26k loss, the IRS doesn't allow you to deduct losses on personal residences even for estates. The selling expenses do reduce the amount realized, but they can't create a deductible loss that flows through to beneficiaries. What I did was report the sale on Form 8949 attached to Schedule D of the 1041, showing the stepped-up basis as the cost basis and the net proceeds (after selling expenses) as the sales price. This resulted in a $0 gain/loss for tax purposes. One thing that helped me was keeping very detailed records of all the selling expenses - not just the realtor commission but also staging costs, minor repairs, attorney fees specific to the sale, etc. Even though they don't create a deductible loss, they do reduce any potential gain if the house had appreciated. Make sure your estate attorney can separate out any fees that were for general estate administration versus the house sale specifically, as those might be deductible as administrative expenses on a different part of the return.

I went through this exact scenario when settling my father's estate two years ago. One additional consideration that hasn't been mentioned yet - if your mother's estate is large enough to require filing Form 706 (federal estate tax return), the treatment of the home sale might have some additional implications for the estate tax calculation. Also, since you mentioned this is your first time as executor, make sure you're aware of the timing requirements. The 1041 is generally due by the 15th day of the 4th month after the estate's tax year ends (typically April 15th if using a calendar year). You can request extensions, but there are specific procedures to follow. One practical tip: if you haven't already, consider opening a separate estate checking account if the proceeds from the home sale will be sitting in the estate for any period of time. Any interest earned would be taxable income to the estate and need to be reported on the 1041. The stepped-up basis rule you mentioned is indeed your friend here - it essentially resets the property's cost basis to the date-of-death value, which typically eliminates most capital gains on inherited property. This is one of the key tax benefits of inherited assets versus gifted assets.