Don't forget to check which payment processor you're using for your taxes! They each charge different rates: Pay1040.com - 1.87% fee (min $2.50) PayUSAtax.com - 1.96% fee (min $2.55) ACI Payments - 1.98% fee (min $2.50) Made the mistake of not checking last year and used the most expensive one. That 0.11% difference adds up on a big tax bill!

Great thread! I'm in a similar situation this year. One thing I'd add is to make sure you factor in the opportunity cost of tying up your credit limits when doing these large tax payments. I learned this the hard way last year when I put $25k on my Amex Gold and then couldn't use it for regular spending while waiting for the payment to process. Had to use my backup cards which didn't have any bonuses running. Also, for anyone considering the Chase cards mentioned here - be aware of Chase's 5/24 rule if you've opened a lot of cards recently. I got denied for the Sapphire Reserve because I had opened 6 cards in the past 24 months, even though my credit score was excellent. One more tip: if you're planning to do this again next year, consider setting calendar reminders to apply for new cards in January/February so you have them ready by April. The application-to-approval process can take weeks, especially for business cards.

Go2Bank holder here and unfortunately can confirm what everyone else is saying - they stick to the exact date on your transcript no matter what. I've been with them for 2 years and they've never released my refund early, even by one day. Since your 846 shows March 27th, that's exactly when you'll get it. I know it's frustrating seeing other banks release early, but at least you know for certain it's coming! The good news is Go2Bank is usually pretty reliable about depositing right at midnight on the scheduled date.

Go2Bank customer for 4 years here - can absolutely confirm they are super strict about the exact deposit date. Never gotten a refund even one day early from them, which is annoying when you see people with Chime getting theirs 3-5 days ahead of schedule. But the silver lining is they're extremely reliable - if your transcript shows March 27th, you can set your alarm for 12:01 AM that day because it'll be there. I've learned to just not even bother checking my account until the exact date to save myself the disappointment. Hang in there, you're almost to the finish line! 🙂

Has anyone used any of the mainstream tax software solutions like Avalara or TaxJar for handling the VDA process? We're trying to decide if we should go with specialized help or if the regular tax software companies have good VDA support.

This is exactly the situation my small manufacturing company went through last year. We had similar issues with high-value products pushing us over nexus thresholds in multiple states despite relatively low transaction volumes. One thing that really helped us was creating a comprehensive spreadsheet documenting every customer interaction regarding exemption certificates. We included dates of requests, methods of contact (email, phone, certified mail), and their responses (or lack thereof). This documentation became crucial during our VDA negotiations. For customers who were clearly resellers but wouldn't provide certificates, we gathered alternative evidence: their business licenses from state databases, screenshots of their websites showing they resell products, and invoices showing consistent business purchasing patterns over multiple years. Several states accepted this as reasonable evidence of exempt transactions. The key insight we learned was that state tax authorities are generally reasonable during VDA processes if you can demonstrate good faith effort and provide logical explanations for why sales were exempt. They understand that businesses sometimes have uncooperative customers. I'd recommend prioritizing your VDA filings by states with the highest potential liability first, and don't let perfect documentation prevent you from moving forward. The penalty relief from VDAs is significant, but only if you act before they contact you.

Has anyone successfully had the IRS accept retroactive loan documentation? My accountant says its too late for me since my business has already made several "repayments" over the last 2 years without proper documentation. Now she wants me to pay capital gains on all of it!

I went through this exact same nightmare last year! My LLC (S-Corp election) had been "repaying" my initial capital injection for two years before I realized I never created proper loan documentation. My CPA initially wanted to treat everything as taxable distributions. Here's what saved me: I worked with a tax attorney to create a formal loan agreement that matched what had actually been happening (reasonable 4% interest rate, quarterly payments). We filed Form 8275 with my amended return explaining the documentation was being formalized to properly reflect the original intent of the transactions. The IRS accepted it without issue. The key was showing that the loan terms were reasonable and consistent with actual business practice. I had to pay tax on the interest portion going forward, but the principal repayments were correctly treated as non-taxable return of my loan. Don't let your CPA take the easy way out by just calling everything capital gains. If you genuinely loaned money to your business with the intent to be repaid, you can usually fix the documentation issue. Just make sure any loan terms you create are commercially reasonable and match what you've actually been doing.

Quick question for anyone who's dealt with this recently - I'm using TurboTax Business for my S-Corp and personal returns. Does it automatically handle the NOL carryforward worksheets and calculations between tax years? Or do I need to manually track this somewhere?

I'm dealing with a similar S-Corp NOL situation and wanted to add some practical tips from my experience last year. Make sure you have good documentation of your stock basis before claiming the loss - the IRS can challenge NOL deductions if you can't prove sufficient basis in your S-Corp stock. Keep detailed records of any loans you made to the company, capital contributions, and prior year income/losses. These all affect your basis calculation and determine how much of the NOL you can actually deduct. I had to reconstruct three years of basis calculations when the IRS questioned my NOL deduction. Also, consider whether the Section 199A QBI deduction might interact with your NOL situation in future profitable years. The interplay between NOLs and QBI can be complex, so it's worth understanding now while you're setting up your tracking systems. One more thing - if your photography business picks up significantly next year, be aware of the potential Section 461(l) excess business loss limitation. It caps business losses at $270,000 for single filers, with excess amounts treated as NOLs subject to the 80% limitation in future years.