How long do we need to keep HSA receipts? Are electronic copies ok or do they need to be original paper receipts?

You should keep HSA receipts for at least 3 years from when you file the return, but I'd recommend keeping them for 7 years to be safe since that's typically how far back the IRS can audit. Electronic receipts are completely fine as long as they show all the relevant information - date of service, provider name, description of service/product, and amount paid. I personally scan all my receipts and save them in a folder labeled by year for easy reference. The IRS accepted my electronic receipts during my audit without any issues.

This is incorrect. You absolutely need to file an amendment with Form 8889 to document your HSA distributions, even if they were all qualified medical expenses. The IRS reconciles your HSA contributions and distributions, and failure to report can trigger an automated notice.

Sometimes it's for tax efficiency, especially for companies that don't plan to go public. LLCs avoid the "double taxation" issue of C-Corps (where profits are taxed at the corporate level, then taxed again when distributed to shareholders). Some tech companies, particularly those that generate significant profits early and want to distribute them, prefer the LLC structure. It's also common in certain sectors like real estate tech or in companies backed by private equity rather than traditional VC. OP, one thing to check - some tech companies use an "Up-C" structure where there's a C-Corp on top for some equity and an LLC underneath for operations. This gets complicated fast, so definitely worth understanding which entity your equity is actually in.

Omg this sounds like a nightmare. Would a regular accountant even know how to handle this or would you need some kind of specialist? I'm getting offered something similar but now I'm wondering if it's worth the hassle.

You definitely need an accountant who specializes in multi-state taxation and pass-through entities. Regular tax preparers often struggle with this complexity. In my case, I ended up using a CPA who specialized in partnership taxation and charged about $2,500 for my tax return that year. Expensive, but worth it since they identified several state-specific deductions I wouldn't have known about. If your equity grant is significant, the tax complexity is probably worth dealing with. But for smaller grants, you have to weigh the potential upside against the added tax preparation costs and headaches.

Thanks for bringing up bonus depreciation! I hadn't even heard of that option. Is there an income limit on bonus depreciation like there is with Section 179? And does the business use still need to be over 50% to qualify?

Bonus depreciation doesn't have the same business income limitation as Section 179, which is why it can be better for freelancers with low income but expensive equipment purchases. You can actually create a loss with bonus depreciation, unlike Section 179. For the business use requirement, you still need more than 50% business use to claim bonus depreciation on listed property (which includes computers and cell phones). If your business use drops below 50% in future years, you may have to recapture some of the depreciation as income, so keep good records of your business vs personal use.

I used TurboSelf-Employed last year for my equipment deductions. It handled basic Section 179 questions okay but didn't really explain the business income limitation clearly. I ended up taking a bigger deduction than I should have and had to file an amended return later. If your situation is complex, it might not be the best option.

Bad idea. I tried that approach with about $8k in stock sales I hadn't reported, and I got a CP2000 notice from the IRS about 8 months later. They automatically added penalties and interest for the "underpayment." It wasn't a full audit, but they definitely caught the discrepancy between my brokerage's reporting and my tax return. Just fix the past returns - it's much less stressful than waiting for them to find it.

Thanks for sharing your experience. That's exactly what I was worried about happening. Did you end up filing amended returns after getting the notice, or did you have to go through some other process to resolve it?

You can absolutely use TurboTax to file amended returns (Form 1040-X). They have a guided process specifically for this. Make sure you have all your 1099-B forms from your brokerage for the years you're amending, as you'll need to complete Form 8949 (Sales and Dispositions of Capital Assets) for each year.

But what if my school didn't send me a 1098-T form? I paid tuition but never got any tax forms. Can I still claim education credits somehow?

You can still claim education credits even if you didn't receive a 1098-T, but you'll need to be able to document your qualified education expenses. Contact your school's bursar or student accounts office immediately and request a copy of your 1098-T. Most schools also make these available to download from your student portal. If for some reason they didn't issue one, keep all receipts showing you paid qualified education expenses. You aren't technically required to attach the form to your return, but you do need documentation in case of an audit. The IRS allows you to claim the credit with alternative documentation of your expenses.

Actually, the OP specifically asked about a 1098-T in the title, not a 1098-E, so people are responding correctly. The confusion about which form is which is exactly the issue here.