5 Have you looked at doing an actual cross-purchase instead of having the company buy back your shares? Sometimes it's cleaner tax-wise to have the other shareholders purchase your shares directly. This avoids any potential accumulated earnings tax issues for the corporation.

11 Whatever you do, make sure to get the stock sale documented properly with a written agreement signed by all parties. I left an S corp a few years back without proper documentation and it was a nightmare when the IRS questioned the transaction later.

Don't forget about state tax requirements too! I found out California recommends keeping records for 4 years from filing date, not 3. Different states have different rules.

Just wanted to add my experience as someone who went through an actual IRS audit last year. I kept 7 years of records and it was MORE than enough. The audit was for my 2021 return (filed in 2022) and they only asked for documents from that specific tax year - nothing older. The auditor told me that unless there's suspected fraud or you drastically underreported income (like 25%+ missing), they rarely need to go back further than the return they're examining. Most audits are triggered by specific items on a particular return, not patterns across multiple years. That said, definitely keep property records until you sell + 3 years like others mentioned. I still have my house purchase docs from 2019 and all improvement receipts because those will matter when I eventually sell. But for regular W-2s, 1099s, and basic tax documents? 7 years has been perfectly fine in my experience.

Has anyone successfully submitted a W9 to [platform name] recently? I heard they updated their system last month and it's been causing problems. I'm wondering if it's a temporary glitch that might be resolved soon.

I had a similar issue recently and it turned out to be a browser compatibility problem! Some platforms' W9 submission systems don't work well with certain browsers or if you have ad blockers enabled. Try switching to a different browser (Chrome if you're using Firefox, or vice versa) and temporarily disable any browser extensions. Also, make sure you're not using autofill for sensitive fields like SSN - sometimes autofill can add invisible characters or formatting that causes submission errors. Try manually typing everything in a fresh browser session. If you're still having issues after trying the platform-specific form that others mentioned, this might be the technical fix you need!

Has anyone mentioned the possible impact to health insurance? When my husband was waiting for disability approval, we had to figure out if him being my "dependent" for health insurance through my job was the same as a tax dependent. It's not! Those are completely different systems.

I just went through almost the exact same situation last year! My husband had been out of work for most of 2023 due to health issues while waiting for his disability determination, and I was so confused about how to handle our taxes. As others have mentioned, you definitely can't claim your spouse as a dependent - that's not how the tax code works for married couples. But filing jointly is almost certainly going to be your best option even with your zero income situation. When we filed jointly, we actually ended up with a larger refund than we would have gotten if I had filed separately, even though he had no income to contribute. One thing I wish someone had told me earlier - if you do get approved for disability and receive backpay, make sure you understand which type of disability benefits you're getting. SSDI backpay gets taxed in the year you receive it (not spread across the years it covers), but the tax impact might not be as bad as you think since you can sometimes use income averaging rules. Also, keep really good records of any medical expenses you've had during this time - they might be deductible and could help offset taxes if you do get a large backpay amount later. Good luck with your disability claim!

bruh moment fr. but srsly tho file that 1040-X quick before they come knockin

Don't panic! I went through the exact same thing last year. Filed my amended return about 3 months after the original deadline and only had to pay a small penalty plus interest (around $150 total on $8k unreported unemployment). The key is getting that 1040-X filed before they send you a notice. Once you file the amendment, you're showing good faith effort to correct the mistake. Way better than waiting for them to catch it first!