Great question about health insurance premiums! You absolutely can document owner's draws specifically for health insurance payments. In fact, I'd recommend being very specific in your documentation - note that it's an owner's draw for "health insurance premiums - self-employed deduction." The key is maintaining that clear separation: the business makes the draw to you as the owner, then you personally pay the health insurance premiums and claim the deduction on your personal return. This approach keeps your business and personal finances properly separated while still allowing you to fund those payments from business profits. Just make sure your LLC shows a net profit for the year, as that's required to claim the self-employed health insurance deduction. If your business has a loss, you can't deduct the premiums that year.

One thing that really helped me avoid commingling issues was creating a simple monthly "owner compensation" process. At the end of each month, I calculate what I need for personal expenses (including estimated tax payments) and take a single owner's draw rather than multiple ad-hoc withdrawals throughout the month. I keep a spreadsheet that breaks down exactly what that monthly draw covers - living expenses, estimated quarterly taxes, health insurance premiums, etc. This way I have clear documentation showing the business isn't directly paying personal expenses, but rather compensating me as the owner, and I'm using that compensation for my personal obligations. This approach has made my bookkeeping much cleaner and gives me confidence that I'm maintaining proper separation between business and personal finances. My accountant loves it because the paper trail is crystal clear if we ever face an audit.

A detailed explanation of what's happening: Early filers are experiencing delays due to the IRS's new fraud detection systems. Blank transcripts typically indicate your return is in the processing queue but hasn't been assigned to a processing team yet. For cycle 05 filers, the best approach is to check your transcripts Friday mornings after the Thursday night updates. I highly recommend using taxr.ai to get a clear picture of your situation - it analyzes your transcript way better than trying to decode it yourself. The tool has been spot on with predicting processing times and identifying potential issues before they become problems.

I'm in the exact same situation! Filed 1/25, cycle 05, three dependents, and my transcripts are completely blank too. It's so frustrating seeing everyone else getting updates while we're just sitting here waiting. I've been checking every Friday morning like clockwork but nothing yet. At least it sounds like we're not alone in this - seems like a lot of early filers are experiencing the same delays this year.

Has anyone used TurboTax Business for filing C-corp returns? Is it manageable for a simple single-member situation like OP's?

I'm in a similar boat - incorporated in January but just realized I missed the 2553 deadline too. After reading through all these responses, I'm definitely leaning toward filing for late relief rather than staying a C-corp for the year. One thing I wanted to add that I learned from my CPA: if you're planning to take significant distributions from the business (beyond just salary), the S-corp election becomes even more valuable because distributions aren't subject to self-employment tax like they would be if you were a sole proprietorship. With a C-corp, those distributions get hit with double taxation. For anyone still on the fence, I'd recommend doing a quick calculation of your expected profit for the year and comparing the tax burden under both scenarios. If you're looking at more than $50K in profit, the late election is probably worth pursuing. The Revenue Procedure 2013-30 process really isn't that complicated - just need to show reasonable cause for the late filing.

try checking your account transcript instead of return transcript. sometimes that updates first

Cycle 05 here too and filed 1/22 - transcript was blank for almost 3 weeks but finally updated this past Friday! Don't stress too much, it seems like they're just really backed up this year. Mine showed up with a DDD of 2/7 so hopefully yours will update soon. Keep checking Friday mornings since that's when cycle 05 typically refreshes 🤞

14 Just a heads up that many CPAs are completely booked for this tax season already. I waited until February last year and ended up having to file an extension because nobody had availability. Might want to start calling around asap!

Great question! I went through this exact same transition a few years ago. You're absolutely right to consider a professional with your more complex situation - rental properties and side businesses have a lot of nuances that TurboTax might miss. To answer your main question: You will still be the one signing your tax return as the taxpayer. The CPA signs as the paid preparer, but you're ultimately responsible for the accuracy of the information. However, a good CPA will have professional liability insurance and should stand behind their work. Here's what typically happens: You'll have an initial meeting where you bring all your documents (W-2s, 1099s, rental income/expense records, business receipts, etc.). They'll prepare your return and then schedule a review meeting to go through everything with you before you sign. This review is crucial - ask questions about anything you don't understand! One tip: Ask potential CPAs about their experience specifically with rental properties and small businesses. Some are more focused on individual returns and might not be as familiar with Schedule E or Schedule C complexities. Also ask about their audit support policy upfront. Start calling soon though - many good CPAs get booked up quickly during tax season!