One thing nobody mentioned is that you should consider setting up an LLC for your DoorDash work! It provides liability protection if anything happens while you're delivering. My cousin got sued when he accidentally damaged something during a delivery.

Great question! I went through this exact situation when I started doing gig work alongside my regular job. Here's what I wish someone had told me upfront: The biggest thing to understand is that you're essentially running a small business now, even if it's just part-time DoorDash. This means you'll need to think like a business owner about taxes and record-keeping. First, open a separate checking account just for your DoorDash earnings and expenses. This makes tracking so much easier come tax time. I learned this the hard way after trying to sort through months of mixed transactions in my personal account. Second, set aside 25-30% of every DoorDash payment immediately for taxes. I know it seems like a lot, but between federal income tax, state tax (if applicable), and the 15.3% self-employment tax, it adds up quickly. Having that money already set aside prevents the shock of owing thousands at tax time. For the quarterly payments - if your W-2 job already withholds enough to cover 90% of your total tax liability (including the DoorDash income), you might not need to make quarterly payments. But it's usually safer to make them anyway to avoid any surprises. One last tip: track your "active delivery time" vs total time. You can only deduct mileage for when you're actually on a delivery or driving to pick up an order, not when you're just sitting in a parking lot waiting for orders to come in. Good luck rebuilding your finances! The extra income from DoorDash can really help, just stay on top of the tax side from day one.

Has anyone tried using any of the tax software packages to track S-corp basis over multiple years? I've been using a spreadsheet but it's getting unwieldy. I've heard QuickBooks doesn't really handle it well, but wondering if any of the tax packages do?

I've been dealing with S-corp basis issues for years and want to clarify something that might help. The ordering rules are actually laid out in IRC Section 1367, and they're pretty rigid: 1. Start with beginning stock basis 2. Add: Income items (including tax-exempt income) 3. Add: Additional paid-in capital contributions 4. Subtract: Distributions (but not below zero) 5. Subtract: Non-deductible expenses 6. Subtract: Losses and deductions So in your case, Henry, your $18.5k additional paid-in capital does create basis that's available for distributions before your current year loss hits. But here's the key detail some people miss - if you take a distribution that exceeds your basis after steps 1-3, that excess becomes taxable as capital gain. One more thing about those suspended losses: they stay suspended indefinitely until you create enough basis to absorb them. They don't disappear, but they also don't factor into the current year ordering calculation. Think of them as sitting in a separate bucket waiting for future basis. Documentation is crucial here. The IRS loves to challenge S-corp basis calculations on audit, so keep detailed records of when you made the capital contribution and any distributions.

I'm having the exact same problem! Been getting that "We are not able to provide assistance to you via the identity verification tool" message for the past 4 days now. It's so frustrating because I've been using that verification portal for years without any issues, and now suddenly I'm completely locked out. What's really annoying is how the error message makes it sound like there's something sketchy about your account when it's clearly just their system being broken. I was genuinely worried for a minute that I'd been flagged for identity theft or something until I found this thread and realized it's happening to tons of people. I tried all the usual troubleshooting - different browsers, clearing cache, using my phone instead of computer, even tried from my friend's house thinking maybe it was an IP issue. Nothing works! At least the regular Where's My Refund tool is still functioning, but you're right that it doesn't give nearly as much detail as the verification portal usually does. Really hoping they fix this soon because I filed electronically on January 31st and I'm getting antsy about my refund status. The fact that the IRS hasn't even acknowledged this is a known issue is pretty disappointing - would it kill them to put up a simple status notice?

I've been experiencing the exact same issue for over a week now! That "We are not able to provide assistance to you via the identity verification tool" error message is so misleading - it really makes you think there's something wrong with your specific account when it's clearly a widespread system problem. What's particularly frustrating is that I've been using the IRS verification portal successfully for the past few years, and now I'm suddenly locked out with no explanation. I filed my return on January 30th, so I'm definitely past the 21-day window, which makes the waiting even more nerve-wracking. Like everyone else, I've tried every possible fix - different browsers, devices, clearing cache, using mobile data instead of wifi - absolutely nothing works. The randomness of who's affected (some people can still access it fine while others are completely blocked) really confirms this is a backend issue on their end. The most annoying part is the complete lack of communication from the IRS about this. A simple status banner saying "identity verification tool temporarily unavailable" would save thousands of taxpayers from panicking and thinking they're being investigated for fraud. Instead, we're all left guessing and turning to forums like this to figure out what's going on. At least the basic Where's My Refund tool is still working, but it's frustrating to lose access to the detailed processing information. Hopefully they get this sorted out soon because tax season stress is bad enough without broken government websites making it worse! 🤦‍♀️

5 One more thing to consider is the new reporting requirements from payment processors. Starting in 2023, platforms like PayPal, Venmo, and eBay are required to send 1099-K forms for anyone with more than $600 in annual transactions. This doesn't change what's taxable (selling personal items at a loss still isn't taxable income), but it does mean you might receive a 1099-K that includes BOTH your business sales AND personal item sales if you use the same account. When you get that form, you'll need to reconcile it on your tax return - reporting your business income on Schedule C while explaining that a portion of the 1099-K amount was from non-taxable personal item sales.

Just to add another perspective - I've been dealing with this exact situation for three years now. One thing that really helped me was setting up completely separate PayPal/eBay accounts for business vs personal sales from the start. My business account handles all the inventory I buy specifically to resell, and my personal account is just for clearing out stuff around the house. When tax time comes, I get separate 1099-K forms and it makes everything so much cleaner to track. If you're already mixing them on the same account, it's not too late to separate going forward. The documentation headache of proving what was personal vs business gets much easier when you can just point to different accounts. Plus it makes your bookkeeping way simpler throughout the year. Also, for those vintage collectibles that might have appreciated - take photos and do a little research on sold listings before you price them. You might be surprised what some of that old stuff is worth, and it's better to know upfront if you're looking at a potential capital gain situation.

I went through this nightmare last year and finally got through! Here's what worked for me: Call the identity verification line (800-830-5084) at exactly 7:00 AM EST on a Tuesday or Wednesday - those seem to be the least busy days. Also, try the "press 0 repeatedly" trick to bypass some of the phone menu. And definitely try the online ID.me verification first if you haven't already - it's way faster than calling if it works for your situation. Hang in there, it's frustrating but you'll get through eventually!

Has anyone had success with the IRS's appointment scheduling system? I saw on their website that you can sometimes schedule a phone appointment for identity verification instead of just calling and waiting on hold. It might be worth checking if that's available in your area - could save you from those brutal wait times! I haven't tried it myself yet but thinking about giving it a shot if the regular phone lines keep being impossible to get through.