Has anyone dealt with a situation where they owned two properties simultaneously? I'm a consultant who splits time between two states about 50/50, own homes in both places, and I'm trying to figure out which one would qualify as my "primary" for Section 121 purposes.

Based on your situation, you have a very good chance of qualifying for the Section 121 exclusion. The key factors working in your favor are that you've maintained all official ties to the property (mail, voter registration, tax returns) and it's your only owned residence. The IRS recognizes temporary absences, even extended ones, as long as there's intent to return. Your digital nomad lifestyle doesn't automatically disqualify you - many people travel extensively while maintaining primary residence status. The fact that you've kept most belongings there and maintained it as your legal address are strong indicators of primary residence. However, I'd strongly recommend documenting everything that connects you to that address before you sell. Keep records of your voter registration, tax filings, bank statements, insurance policies, and any other official documents tied to that address. This documentation will be crucial if the IRS ever questions your claim. One potential complication is the partial rental situation you mentioned in the comments. Make sure you're properly accounting for any rental income and be prepared to allocate the exclusion based on the percentage of the home used for personal versus rental purposes. But this shouldn't disqualify you entirely - just affects the calculation. Given the complexity and potential tax savings involved, it might be worth consulting with a tax professional who can review your specific situation and ensure you're maximizing your exclusion while staying compliant.

For what it's worth, I think there's a reasonable middle ground here. The technical IRS answer is that your regular coffee is probably a personal expense, BUT if you're actually using these coffee shops as your main workspace (like you described), you might consider tracking your total expenses at these locations and categorizing them as "temporary workspace rental" rather than specifically "coffee." Many freelancers and ICs who don't have dedicated offices do this, especially if they have documentation showing they conducted business there (calendar appointments, work product created, etc.). It's less about the coffee itself and more about the cost of having a place to work. Whatever you decide, just be consistent and have good documentation!

As someone who's been freelancing for about 3 years now, I can relate to this question! I've found that the key is really in how you frame and document the expense. What I do is keep a detailed business journal where I log my "mobile office" expenses. Instead of just writing "coffee - $4.50," I write something like "Workspace rental at Blue Bottle Coffee, 4 hours client work on ABC project, purchased required beverage for table use - $4.50." I also take a quick photo of my laptop setup at the coffee shop with the receipt nearby. It sounds a bit extra, but it creates a clear business narrative if anyone ever questions it. The IRS cares more about the business purpose than the specific item purchased. That said, I'm conservative and only deduct about 75% of these expenses, treating the remaining 25% as personal enjoyment of the coffee itself. This approach has worked well for me, and my tax preparer says it shows good faith effort to separate business from personal expenses. Just remember to be consistent whatever approach you choose - don't deduct coffee shop visits on some days but not others if you're doing the same type of work!

Has anyone actually gotten TurboTax to let them enter this correctly? I've been using TT for years and don't want to switch, but I'm in the exact same PEO situation and can't figure out how to override it.

I'm dealing with this exact same situation right now! My company switched to a PEO mid-year and I'm seeing the same overwithholding issue. Reading through all these responses is super helpful. Quick question for those who've been through this - when you calculate the excess amount for Schedule 3 Line 11, do you use the current year's Social Security wage base limit? I want to make sure I'm using $160,200 for 2023 (which would make the max withholding $9,932.40) and not some other figure. Also, has anyone had success with the TurboTax workaround that Landon mentioned? I'm using TurboTax Deluxe and want to try that route before attempting the double W-2 entry method. Thanks everyone for sharing your experiences - this thread is a goldmine for PEO tax issues!

Make sure you're thinking about estimated taxes too! With such a big income jump, your withholding might not cover everything, especially with two jobs. If you end up owing more than $1,000 when you file, you could face underpayment penalties. You can avoid this by either: 1) Withholding at least 90% of what you'll owe for the current year, or 2) Withholding at least 100% of what you owed last year (110% if your AGI was over $150,000). The second option is probably easier for you since your income last year was much lower. Just make sure your total withholding exceeds your 2022 tax liability and you should avoid penalties!

Congratulations on the huge income jump! That's an incredible achievement. A few additional thoughts to consider: Since you mentioned you're married as of June, make sure you update your filing status considerations. If your spouse also works, you'll want to coordinate your withholdings together to avoid surprises. The "married filing jointly" vs "married filing separately" decision could impact your overall tax strategy. Also, with $40k in student loans, don't forget about the student loan interest deduction! You can deduct up to $2,500 in student loan interest paid during the year, which phases out at higher incomes but you should still qualify at $120k combined income. One more thing - consider setting up automatic transfers to a separate savings account specifically for taxes. Even if you get your withholding perfect, it's good practice to have a tax buffer fund. Maybe start with $200-300 per month until you get a better handle on your actual tax liability. Better to be prepared than scramble to find money at tax time! The tools others mentioned (TaxR.ai for planning, Claimyr for IRS contact) sound helpful, but also consider meeting with a CPA for your first year with this income level. They can help you set up systems and strategies that will serve you well going forward.

Happened to me last year. Quick fix: file a new W-4 and put an additional amount to withhold on line 4(c). Calculate what you should be paying per paycheck and add a little extra to catch up on what you've missed. I use the IRS Withholding Calculator to figure out the right amount. Makes it super simple. Better to fix it yourself than wait for HR, tbh. Most payroll people aren't tax experts.

This is definitely a red flag that needs immediate attention! I went through something similar at my first job out of college and it's so stressful when you're just starting out. Here's what I'd recommend doing right away: 1. Contact your HR/payroll department first thing tomorrow with your W-4 copy in hand. Ask them to verify how your information was entered into their system. 2. If they can't fix it immediately, ask for a timeline of when it will be corrected. Document this conversation in writing (email follow-up). 3. Keep detailed records of every paycheck showing the missing withholding - you'll need this if there are any issues later. At $62k annually, you should expect roughly $200-300 in federal taxes withheld per paycheck depending on your pay frequency. The fact that they got Social Security and Medicare right suggests it's likely just a data entry error rather than something more concerning. If your employer drags their feet on fixing this, don't wait - you can always submit a new W-4 with additional withholding amounts specified to ensure you're covered going forward. Better safe than sorry when it comes to taxes!