Anyone know if the tax treatment is different for qualified vs non-qualified dispositions of ESPP shares? I've held mine for over a year but less than 2 years from the offering date.

This is exactly the kind of confusion that trips up so many ESPP participants! You're right to be concerned about double taxation, but the good news is that you've already paid the taxes on that $135. Here's what happened: When you acquired the shares in August 2023, the $135 "bargain element" (the discount you received) was treated as compensation income and included on your W2. You paid ordinary income tax on this when you filed your 2023 return. When you sell in 2024, your cost basis for tax purposes will be the fair market value of the shares on the purchase date (8/15/23) - which already includes that $135 discount that was taxed. So you'll only owe capital gains tax on any appreciation since then. Make sure your broker reports the correct adjusted cost basis on your 1099-B. Sometimes they get this wrong and show a lower basis, which could lead to overpaying taxes. If there's a discrepancy, you'll need your ESPP statements to prove the correct basis. Since you're planning to use TurboTax, it should handle this correctly as long as the 1099-B shows the right cost basis. Good luck with those home repairs!

Great advice from everyone here! As someone who recently went through this exact situation in Washington, I'll add that the IRS withholding calculator is definitely your best bet for accuracy. One thing I learned the hard way - if your restaurant job pays tips, make sure to account for those in your calculations too. Tips are taxable income but often have minimal withholding, which can throw off your entire withholding strategy if you don't plan for them. Also, since you mentioned you've always done "single, zero" in the past, you might want to double-check that you haven't been overwithholding on your main job all these years. With the new W-4, you could potentially increase your take-home pay while still withholding the right amount across both jobs. The calculator will show you different scenarios - I found it really helpful to run it a few times with conservative and optimistic estimates for my variable restaurant income to see the range of outcomes.

Just went through this exact situation last month when I started bartending on weekends while keeping my full-time office job. Here's what worked for me: I used the IRS withholding calculator first to get a baseline, then cross-referenced it with the Multiple Jobs Worksheet on the W-4. Both gave me similar results, which was reassuring. For my main job, I updated my W-4 to account for the additional income using the calculator's recommendations. For the bartending job, I kept it simple - filled out just the basic info in Step 1 and signed it in Step 5, leaving Steps 2-4 blank. This withholds at the higher single rate on that income. One tip: since restaurant work often involves tips (which have minimal withholding), I also added a small additional withholding amount on line 4(c) of my weekend job's W-4. Started with $25 per paycheck and adjusted after a few weeks once I had a better sense of my actual tip income. The key is you can always submit an updated W-4 if you need to adjust. Better to start conservative and tweak it than get hit with a surprise tax bill next year!

Your best bet is to submit a W-4 with your information so they can properly pay you as an employee. If you're concerned about identity theft, monitor your credit reports after giving them your SSN. You can get free credit reports at AnnualCreditReport.com and even put a fraud alert on your accounts if you're really worried.

Unfortunately, paying training shifts "under the table" is illegal, even though it's common in the restaurant industry. All hours worked, including training time, must be properly documented and paid through payroll with appropriate tax withholdings. The fact that multiple restaurants have done this doesn't make it legal - it just shows how widespread wage violations are in food service. Employers often justify this by saying training shifts are "unpaid" or "trials," but the Department of Labor is clear that if you're performing any work that benefits the business, you must be compensated as an employee. This is exactly why you should be cautious about the restaurant in your original post. Places that cut corners on basic employment law (like proper payroll processing) often have other violations too. Document your hours worked and consider filing a wage complaint with your state's labor department if they won't pay you properly.

Ok this might sound dumb but I had a similar issue and realized I was looking at an outdated form. Double check you have the 2024 version of Form 8959? They made some changes to the Additional Medicare Tax calculation in recent years. Also check if ur tax software is up to date. TurboTax automatically updated for me mid-filing season last year cuz there was some correction to one of the forms.

I've been dealing with Form 8959 for several years now and you're not going crazy - there have definitely been some confusing aspects to the Additional Medicare Tax calculations. The most common issue I see is with Line 22 when people have income right around the threshold amounts. One thing that might help: make sure you're using the most current version of both the form and instructions. The IRS has made several revisions over the years, and sometimes the earlier versions had calculation errors or unclear guidance. For your situation with $275k income as a single filer, you should be calculating Additional Medicare Tax on the amount over $200k. If the worksheet is giving you a different result than what seems logical, try working backwards from the tax code itself - Section 1411 of the IRC is pretty clear about the 0.9% rate on income exceeding the threshold. Document your calculation method thoroughly regardless of which approach you take. If there really is an error in the form instructions, having clear documentation of your reasoning will protect you later.

Another expense to consider - property taxes during the renovation period. Unlike loan interest and utilities which can potentially be capitalized, property taxes are generally deductible on Schedule A (if you itemize) rather than being added to basis. This is true even during the renovation period. Also, make sure you're separating any personal use from the renovation timeline. If you stayed in the property at any point during renovations, you'll need to allocate expenses accordingly. The IRS is pretty strict about this - only expenses incurred while the property was held purely for investment/sale purposes can be capitalized. One last tip: keep photos documenting the before/during/after condition of the property. This helps support your position that certain expenses were truly improvements rather than just repairs or maintenance.

One thing that hasn't been mentioned yet - if you had to get any permits for your renovation work, those permit fees can definitely be added to your basis as they're directly related to the improvements. Same goes for any required inspections. Also, be careful about mixing renovation expenses with regular maintenance. For example, if you had to replace a broken window during renovation, that's maintenance/repair. But if you upgraded all the windows to energy-efficient ones as part of improving the property, those are capital improvements that increase your basis. The key test is whether the expense restores the property to its original condition (repair/maintenance) or makes it better than it was (improvement). For a flip, you're generally trying to improve the property beyond its original state, so most of your major expenses should qualify for basis treatment. Keep all your receipts organized by category - it'll make everything much easier come tax time!