Have you actually used OLT yourself? I've never heard of them before and I'm worried about using some random tax site. Are they an authorized IRS e-file provider? And did they handle the rest of your taxes okay? I've got some investment stuff and a small business too.

Yes, I've used OLT for the past two years including this year with Form 7202. They are definitely an authorized IRS e-file provider - you can check the IRS website for their list of authorized providers and OLT is on there. For your investment and small business concerns, they handled my stock trades and side gig income without any problems. Their interface isn't as slick as TurboTax, but all the necessary forms and schedules are there. I found their small business section particularly good at walking through deductions many people miss. The $49.95 price includes all forms including Schedule C for business.

I'd love to use a professional but am worried about the cost. Did you shop around for EAs or just pick one? $275 actually sounds reasonable - I was quoted $450 by someone local and thought that was the going rate. Also, how did you find them?

Wouldn't traditional IRA be better if they're trying to lower their current tax bill though? Roth doesn't help with that at all.

You're right that a traditional IRA would help lower the current tax bill, which is definitely an advantage if immediate cash flow is the primary concern. I suggested Roth because at $65k, OP is probably in the 22% tax bracket now, and many financial planners believe this is a relatively favorable rate to pay taxes at, especially for someone early in their career whose income (and potentially tax bracket) will likely increase. The long-term tax-free growth often outweighs the current tax deduction for younger earners. But it's definitely a personal decision that depends on individual circumstances and priorities.

The new W-4 doesn't use allowances anymore (changed in 2020). You now have to specify actual dollar amounts for additional withholding or reduction. Bit more complicated but more accurate.

Thanks for the correction! Shows how long it's been since I updated mine. Guess I need to look at the new form and figure out what numbers to put in there. Appreciate the info!

That's a really good point I hadn't considered. I did file pretty early (mid-February) because I usually get a refund. I'm going to log into my brokerage account right now and see if they issued a corrected 1099-B that I missed. If they did, would I need to file an amended return or just respond to the notice with the updated information?

You typically don't need to file an amended return in this case. The response to the notice effectively serves as your correction. In your response letter, you should explain that you filed with the original information provided by your brokerage, and include copies of both the original and corrected 1099-B forms. Make sure to clearly reconcile the differences between what you reported and what the corrected form shows. The IRS mostly wants to see that you can account for the discrepancy and that you're not trying to hide income. They're generally reasonable when the error originated with the brokerage rather than you.

Online response is definitely better when available! But you still need to scan and upload all your supporting documents. I did mine online last year and still had to upload about 20 pages of stock transaction records. But processing time was only about 3 weeks versus the 2+ months it took when I mailed in a response the previous year.

You make a good point about still needing to provide all the documentation. I should have been clearer. The main advantage isn't reducing what you need to submit, but rather the processing time and confirmation. When you submit online, you get an immediate confirmation that they received your response, which gives peace of mind compared to wondering if your mail got lost. The other major advantage is that online responses typically get processed in the order received, while paper responses can get shuffled into various processing backlogs. This is especially important when responding to a notice with a deadline.

How do you prove mileage if you get audited? I've been taking pics of my odometer before and after shifts... is that enough?

A mileage log is your best bet. You don't need to take pics of your odometer (though it doesn't hurt), but you should record the date, starting location, ending location, purpose of the trip, and total miles driven. There are free apps that can help track this automatically. The IRS mostly wants to see that you have a consistent record-keeping system, not just estimates after the fact. Even a simple spreadsheet or notebook works as long as you update it regularly. If you claim a ton of miles with zero documentation, that's when audit flags can pop up.

While technically all income should be reported, the practical reality is that the IRS is not going to come after you for a few dollars in tax on $38. DoorDash won't issue any tax documents for this amount. That said, it's generally best to develop good tax habits from the start. If this is your only income, you likely wouldn't even need to file. If you have other income requiring you to file anyway, including the $38 is the right thing to do, but realistically, the impact on your tax bill will be minimal and the chances of issues arising from omitting it are extremely low.

Thanks for this advice! Looking at my notice now, I think there might actually be both types of penalties. Would I be eligible for FTA on both the late filing and late payment penalties? Or just one of them?

You can absolutely request First Time Abatement for both penalties! The FTA can cover failure-to-file, failure-to-pay, and failure-to-deposit penalties. Just make sure to specify in your request that you're asking for abatement of all penalties assessed for that tax year. Many people don't realize that multiple penalties can be covered under a single FTA request, as long as they're all for the same tax period. The important thing is to clearly identify all the penalty types in your request so nothing gets overlooked.

I tried using the online account for this last year and couldn't find any way to submit a penalty abatement request. Ended up having to call. The online services seem limited to viewing your account, making payments, and getting transcripts.