19 Has anyone used TurboTax to handle this RSU situation? I've got a similar problem and wondering if it can handle the cost basis adjustments properly.

I'm dealing with a very similar RSU tax situation right now! My employer also liquidated some of my vested shares and I'm getting that same confusing 1099-B with no cost basis reported. It's so frustrating because it makes it look like I owe taxes on gains I never actually realized. From what I've been reading in the IRS publications, you're absolutely right that the vesting date FMV should be your cost basis. The key thing is that when RSUs vest, that fair market value gets added to your W-2 income, so you've already been taxed on that amount. Your actual capital gain or loss is just the difference between what the shares were worth when they vested versus what they sold for. One thing I learned is to make sure you save all your documentation - not just the CSV from your brokerage, but also any supplemental tax documents your employer provided about the RSU transactions. Some companies send additional forms or statements that help clarify the cost basis calculations. Have you checked if your employer's HR or benefits team has any resources to help with this? Mine had a tax guide specifically for RSU reporting that I found really helpful.

One important thing to keep in mind is the timing of when you establish residence vs when you start claiming it as your primary residence for tax purposes. The IRS looks at where you actually live for the majority of the year, so if you're renovating for 3-4 months while still renting in town, you'll want to be careful about when you officially claim the cabin as your primary residence. I'd suggest keeping detailed records of when you actually move in full-time (utility hookups, mail forwarding, voter registration change, etc.) and use that date as your official residence change date for tax purposes. Don't try to claim it as primary residence while you're still primarily living in the apartment - that could create issues if audited. Also, since you mentioned this is raw land, make sure the cabin renovation meets local building codes for habitable structures. The IRS generally expects a primary residence to be a structure suitable for year-round occupancy with basic amenities (plumbing, electricity, heat). Document the improvements you make to ensure it meets these standards.

This is a great question and I can see you've gotten some solid advice already! Just wanted to add a few points from someone who went through a similar process last year. One thing I learned the hard way is to document EVERYTHING from day one. I created a simple spreadsheet tracking all expenses (renovation materials, utilities, loan payments, etc.) and categorized them as either "personal residence" or "farm business" related. This saved me tons of time at tax season and would be crucial if ever audited. Also, regarding the mortgage interest deduction - keep in mind that with the current standard deduction being so high ($13,850 for single filers in 2023), you might not benefit from itemizing unless you have other significant deductions. Run the numbers both ways to see what actually saves you more money. One last tip: consider consulting with a tax professional who specializes in agricultural properties before you finalize your setup. The upfront cost is usually worth it to make sure you're structuring everything optimally from the start, especially with the complexity of mixed-use property. Better to get it right initially than try to fix it later! Good luck with your farm venture - sounds like an exciting project!

I'm going through something similar right now and this thread has been incredibly helpful! I got the same withholding verification letter about 10 days ago and have been trying to reach the IRS ever since. Based on what everyone's shared here, it sounds like having all your documentation ready is key - I've already organized all my W-2s and made copies of everything. I'm also going to look into both the taxr.ai service that several people mentioned for document analysis and possibly Claimyr to help get through to an actual agent. The in-person appointment idea is really smart too - I didn't even know that was an option. Does anyone know if the local offices can handle these withholding verification issues, or do they typically need to escalate to a different department? Really appreciate everyone sharing their experiences. It's reassuring to know this is a common issue that usually gets resolved once you can actually talk to someone!

I'm dealing with a similar withholding verification issue right now and this whole thread has been a lifesaver! I got my letter about 2 weeks ago and have been stressing about it constantly. What's really frustrating is that I know my numbers are correct - I've checked them multiple times against my W-2s. But reading everyone's experiences here makes me feel so much better knowing this is actually a common system issue and not something I did wrong. I'm planning to try the combination approach that several people mentioned - using taxr.ai to get my documentation analysis ready, then trying Claimyr to actually get through to an agent. If that doesn't work, I'll definitely look into scheduling an in-person appointment at my local office. The part about keeping detailed records of all contact attempts is really smart advice too. I've already started a log with dates and times of my failed call attempts. Thanks to everyone who shared their stories - it's so helpful to know there's light at the end of the tunnel with these IRS issues!

One thing nobody's mentioned yet - make sure you're tracking EVERYTHING related to these educational expenses, not just the tuition itself. If you traveled to take the courses, those travel expenses might be deductible too. Same with required books, supplies, software, etc. I deducted about $5,300 in education expenses for my consulting business last year, and almost $1,200 of that was actually the supplementary costs beyond just the course fees. My accountant said as long as they're necessary for the education that improves your current business skills, they should qualify.

Has anyone used TurboTax Self-Employed for handling these kinds of business education deductions? I'm trying to decide between that or hiring a CPA this year, especially with these education expenses I want to deduct.

Has anyone mentioned just banking the money in a regular business account? I run a small business and sometimes just leave profits in my business checking account until the next year when I need them. The money still shows up as income on my taxes, but at least I have the cash available for later.

One option that hasn't been fully explored here is setting up a Solo 401(k) if your consulting work qualifies as self-employment income. With a Solo 401(k), you can contribute both as the employee ($23,000 for 2025, or $30,500 if over 50) AND as the employer (up to 25% of compensation). This could potentially allow you to defer a significant portion of that $65k. The key is that your consulting income would need to be structured as self-employment rather than W-2 income from the client. You'd also want to make sure you're not exceeding the overall 415(c) limit when combined with your main job's 401(k). Another approach worth considering is a defined benefit plan if your consulting income is substantial and consistent - these can allow much higher contribution limits than traditional retirement accounts, sometimes $200k+ annually depending on your age and income projections. I'd strongly recommend getting professional advice before implementing any of these strategies, as the rules can be complex and mistakes can be costly.