WATCH OUT with these repayments! I did something similar and didn't realize there were SPECIFIC CODES that needed to be used when repaying. My repayment got coded as a regular contribution instead of a rollover/CARES repayment, and it caused a huge headache with both the IRS and my tax filing. Make sure whatever financial institution you use for the repayment understands it's specifically a CARES Act repayment. Get written confirmation of how they coded it. Also, keep ALL your documentation showing the original distribution and the repayment for at least 7 years - I got audited on mine and was glad I had everything.

This is exactly why I love this community - so many helpful real-world experiences! I'm dealing with a similar situation but with a twist. My wife took her CARES Act distribution in late 2020, and we're now in 2023 getting close to that 3-year deadline. One thing I haven't seen mentioned yet is the timing aspect. Since you spread the income over 3 years (2020-2022), make sure you understand which tax years you'll need to amend. If you repay before the end of 2023, you can still file amended returns for all the years you reported the income. Also, I called my local IRS Taxpayer Assistance Center and they mentioned that some people are running into issues where their original 401k providers are claiming they can't locate the distribution records from 2020. Might be worth getting copies of all your original distribution paperwork from Fidelity before you start the repayment process, just in case you need to prove the connection between the original distribution and your repayment. The clock is ticking for all of us 2020 CARES Act folks, so definitely don't wait much longer!

Has anyone used HR Block or TurboTax to figure out the right withholding? The IRS calculator gives me anxiety with all those fields.

I've been dealing with a similar situation and found that the key is to be methodical about it. Here's what worked for me: First, gather your last year's tax return and recent pay stubs. Calculate your effective tax rate from last year (total tax ÷ total income) and apply that to your current year's expected income. This gives you a baseline for what you should owe. Then compare that to what's already being withheld from both paychecks combined. The difference is roughly what you need to add in extra withholding. For your $245K combined income, an effective tax rate around 18-20% is reasonable (depending on deductions). So you'd expect to owe about $44K-49K total. If your current withholding is only covering $38K-39K, then yes, you'd need that extra $5K-6K in withholding. Regarding who should have the extra withholding - it truly doesn't matter for tax purposes since you file jointly. However, I'd suggest having the higher earner do most of it simply because their payroll system is already handling larger withholding amounts, so adding more won't be as noticeable percentage-wise. Start with $250 extra per paycheck and monitor it quarterly. You can always adjust mid-year if needed.

Something else to consider: insurance costs differ significantly between short-term and long-term rentals. I pay about 60% more for insurance on my Airbnb property vs my long-term rental. This is deductible, but affects your bottom line. Also, if you're comparing profitability, remember to account for vacancy rates with short-term rentals and management fees if you're not handling everything yourself. These factors can drastically change which option makes more financial sense after taxes.

Great discussion everyone! As someone who's been through this exact decision, I'd add that you should also consider the depreciation recapture implications long-term. With short-term rentals classified as business income, you might face different recapture rules when you eventually sell the property compared to long-term investment property. Another factor that helped me decide: cash flow timing. Short-term rentals give you more frequent income but also more frequent expenses (cleaning, restocking, maintenance between guests). Long-term rentals are more predictable but you're stuck if you get a problem tenant. Given your $95k salary, you might also want to look into whether you qualify for real estate professional status if you go the short-term route and put in enough hours. This could potentially allow you to deduct rental losses against your W-2 income, though the requirements are pretty strict (750+ hours annually in real estate activities). One last tip: whichever route you choose, set up a separate business checking account from day one. Makes bookkeeping and tax prep so much easier, and the IRS likes to see clear separation between personal and rental activities.

Has anyone considered that the IRS might get data from financial institutions? Like if you're regularly transferring money from FanDuel to your bank account, those deposits could potentially be flagged, especially if they add up to significant amounts.

The bottom line is that ALL gambling winnings are taxable income, period. It doesn't matter if FanDuel sends you a form or not - you're legally required to report that $9,500 on your tax return. FanDuel's customer service rep was technically correct that your winnings don't meet their threshold for issuing tax documents, but they were wrong to imply this means it's not taxable. Sports betting platforms only issue W-2Gs when specific conditions are met (usually $600+ winnings that are at least 300x the original wager), but that's about THEIR reporting requirements, not YOUR tax obligations. You need to report this as "Other Income" on Schedule 1 of your tax return. Make sure you keep detailed records of all your betting activity - wins AND losses - because you can deduct gambling losses up to the amount of your winnings if you itemize deductions. Don't risk it by not reporting. The IRS has been cracking down on unreported gambling income, and with electronic payment trails it's easier than ever for them to discover unreported winnings during audits or through data matching programs.

This is such valuable information, thank you for sharing! I'm currently dealing with something similar with TickPick - they've been sending me emails for about 2 weeks requesting my SSN after I sold some football tickets for $145 total (actually less than what I originally paid since I had to price them to sell quickly when I found out I couldn't attend). Reading through all these experiences has been incredibly helpful. I was starting to feel guilty about ignoring their emails, especially with subject lines like "Action Required for Tax Reporting" that made it sound so official and urgent. But seeing how consistent everyone's experiences have been across different platforms really validates my instinct that something wasn't right about providing my SSN for such a small personal transaction where I actually lost money. The tax professional's explanation about the $600 threshold and profit requirements was particularly enlightening - it's clear my situation doesn't come close to meeting any IRS reporting obligations. What bothers me most is how these platforms use official-sounding language to pressure people into giving up sensitive personal information when it's not actually required for most personal ticket sales. Your success story gives me confidence to continue waiting it out rather than cave to their pressure tactics. It's amazing how many people are dealing with this exact same issue - really shows these are standardized corporate data collection strategies rather than legitimate tax requirements. Thanks for helping all of us realize we have the right to protect our personal information while still following actual tax law!

This thread is incredibly helpful! I've been dealing with a similar situation with Ticketmaster for the past 3 weeks. They keep emailing me requesting my SSN for selling a pair of concert tickets at face value ($240 total) that I couldn't use due to a work conflict. Like many others here, those emails with urgent language made me feel like I was required to comply immediately, but something felt off about sending such sensitive information via email for a straightforward personal transaction with zero profit involved. Reading everyone's real experiences - especially seeing how consistently these refunds get processed automatically across different platforms - gives me so much confidence to wait it out rather than cave to their pressure tactics. The tax professional's explanation about the $600 threshold and profit requirements really clarified that my situation doesn't even come close to triggering any IRS reporting obligations. It's eye-opening to see how widespread this issue is and how these platforms use the same intimidation strategies regardless of whether your specific transaction actually requires any additional reporting. Thanks to everyone who shared their experiences - this is exactly the kind of community support that helps people make informed decisions about protecting their personal information while still following legitimate tax requirements!