Be careful with the standard mileage deduction! If you're going to use it, you need to have started using it in the first year of putting your vehicle into service for business. If you claim actual expenses the first year, you're stuck with that method for the life of the vehicle.

I'm dealing with a similar situation right now! For what it's worth, I found that keeping simple records going forward makes a huge difference. Even if you can't reconstruct everything perfectly from the past, you can at least get organized for the rest of 2024. One thing that helped me was going through my bank statements and delivery app earnings summaries to piece together what I could remember about expenses. Even rough estimates are better than nothing, and the IRS generally accepts reasonable approximations when you can show you made a good faith effort. The key thing is don't let this overwhelm you - lots of gig workers go through this exact same learning curve. The important part is getting compliant going forward and addressing the past issues systematically. You've got this!

Have you considered alternating years? That's what my ex and I do - I take odd years, he takes even years. No Form 8332 needed if you follow the tie-breaker rules and have it specified in your custody agreement. Saves a lot of paperwork and potential disputes. We just make sure our custody agreement clearly states which parent claims the child in which years, and then we each take the exemption, Child Tax Credit, and any medical expenses we personally paid in our designated years. Much simpler than dealing with Form 8332 every year.

As someone who went through a similar situation with significant medical expenses for my child, I can share what I learned from both my tax preparer and direct experience with the IRS. The key insight that helped me was understanding that Form 8332 creates a very specific split of benefits - it ONLY transfers the dependency exemption and Child Tax Credit to the non-custodial parent. Everything else stays with whoever is entitled to it under normal rules. For your medical expenses specifically, you can deduct them if YOU paid them, period. The IRS doesn't care who claims the dependency exemption when it comes to medical expense deductions - they only care who actually wrote the checks or used their credit card. I claimed $3,200 in medical expenses for my daughter even though my ex claimed her as a dependent that same year. No issues whatsoever. Just make sure you have solid documentation (receipts, insurance statements, etc.) showing you were the one who paid. One tip: if you're close to the 7.5% AGI threshold for medical deductions, run the numbers both ways to see if it makes more sense for you or your ex to claim the medical expenses, assuming you both contributed to the costs.

Another option is to e-file now WITHOUT the Form 2210 and then file an amended return later with Form 2210 once it becomes available. This gets the main return processed right away, clearing any employer holds, and then you deal with the penalty waiver separately.

You're absolutely right to be concerned about this timing issue! Form 2210 availability delays are unfortunately common, especially early in filing season. I've been preparing returns for over 15 years and see this almost every year with certain specialty forms. Here's what I'd recommend based on your situation: Since your clients have employer pressure and potential bonus issues, I'd suggest calling the IRS practitioner hotline (if you have a PTIN) to get official guidance on whether you can e-file with a statement explaining the Form 2210 delay, then submit the actual form later. Some years they've allowed this approach. If that's not possible, paper filing might be your best bet despite the longer processing time. The key is properly documenting the penalty waiver circumstances - make sure you have all supporting documentation for casualty losses, disasters, or unusual circumstances that prevented normal estimated payments. Also, definitely provide that employer letter as others mentioned. I usually include language confirming the return is complete except for IRS form availability issues beyond our control. Most employers understand this isn't the taxpayer's fault. Keep checking your software for Form 2210 updates - they sometimes release forms with little notice during peak season!

I'm going through the exact same thing right now! Got my 60-day letter back in December and here we are in February with still no movement. It's so frustrating especially when you're counting on that money. I've been checking my transcript weekly but it just shows the same review status. Really hoping we all get some good news soon 🤞

I'm in a similar situation - got my 60 day letter back in late December and still waiting. What's really helped me is setting up text alerts through the IRS2Go app so I get notified immediately if there are any updates to my refund status. Also been checking my account transcript every Friday just to see if anything changes. It's definitely nerve-wracking when you're depending on that money, but from what I've read here and other places, most people do eventually get their refunds, it just takes way longer than the initial 60 days they quote. Hang in there! 💪

Don't forget you also need to pay yourself a reasonable salary as an S-corp owner!!! The IRS watches this closely. You can't just take all distributions and no salary to avoid payroll taxes. My friend tried that and got audited.

Just went through this exact situation with my consulting LLC that elected S-corp status! After all the confusion, here's what I learned: You definitely need Form 1040-ES for your personal estimated tax payments. Since you're a single-member LLC with S-corp election, the business profits flow through to your personal return, so you make estimated payments as an individual. The 1120-W would only apply if your S-corporation itself owed taxes (like built-in gains tax), which is rare for small businesses like ours. One thing that helped me was calculating my estimated payments based on last year's tax liability using the safe harbor rule - if you pay 100% of last year's taxes (or 110% if your AGI was over $150K), you won't face penalties even if you owe more this year. Also make sure you're withholding enough from your S-corp salary for payroll taxes. The estimated payments with 1040-ES should cover the income tax on your distributions, but your salary withholding needs to handle that portion separately. Hope this helps while you wait for your accountant to return!