10 Do you think it's worth paying for quarterly meetings with a CPA if my business is still pretty small (making around $45k annually)? Or is that overkill at this stage?

2 At $45k annual revenue, quarterly CPA meetings might be a bit much unless your business has unusual complexity. At that stage, I'd suggest an initial consultation with a CPA to set up your structure and accounting system correctly, then perhaps semi-annual check-ins (mid-year and year-end). Many small business owners at your stage do well with a solid tax preparer who has small business experience for the actual tax filing, combined with good bookkeeping software you maintain throughout the year. The key is keeping organized records all year, not scrambling at tax time. That approach gives you most of the benefits without the full CPA cost until your revenue justifies the added expense.

19 I've never even heard of an Enrolled Agent! Are they allowed to represent you in an audit like a CPA can? How do you find a good one?

That's actually a really good idea I hadn't thought of. I believe the owner's sister is handling his affairs, but honestly we've all been keeping our distance out of respect while she's grieving. Maybe I could reach out carefully and just ask if she has any information about the business accounts or records. The restaurant was doing well financially, so there must be some kind of bookkeeping or records somewhere.

Approaching with sensitivity is definitely the right move. You might frame it as wanting to properly close out your employment relationship with the business rather than just tax documents. The executor likely has legal access to business records that could help everyone involved. If there was a business accountant or bookkeeper separate from Paycom, they might also have records that would be helpful. Many businesses keep separate financial records beyond what their payroll service maintains.

This is 100% the way to go. I worked payroll for years and the YTD on your final December paystub should match your W2 exactly for most regular employees. Only difference might be if you had taxable benefits added after the last payroll was processed.

Thanks for this suggestion! I actually tried asking if they would accept proof of application but they were pretty firm about needing the actual ITIN before finalizing the lease. I didn't think about the occupant vs. lease-holder distinction though - that's a really good idea. I'll check if my income alone meets their requirements. The only concern is that many places have rules about all adults living in the unit being on the lease. I'll definitely bring this up with them tomorrow. Really appreciate the suggestion!

They use it for identity verification and for potential collections if you break the lease. Without an ITIN or SSN, they have no way to report to credit bureaus or track you down if you skip out on rent. Some places will accept a larger security deposit instead.

That makes sense, thank you. I hadn't considered the collections angle. I wonder if offering an additional security deposit might work in the original poster's case. Seems like that would address their concern about potential risk.

Do you have to wait until they assess the penalty before requesting abatement? Or can you be proactive and request it when you file?

You generally need to wait until they assess the penalty before requesting abatement. The IRS typically sends a separate notice about penalties after processing your return. When you get that notice, that's when you should call and request the First Time Penalty Abatement. You can't really request it proactively when filing because the IRS needs to calculate the penalty first. The good news is that if you qualify, they'll usually grant it without much hassle as long as you've had a clean compliance record for the previous 3 years.

This is such a good point. I'm in California and their underpayment penalties are actually worse than the federal ones. Had to pay almost 9% penalty on what I owed to the state.

That's really helpful - I was so focused on figuring out the correct amount that I hadn't thought about the deadline. The notice says I have 30 days to respond. If I request more time, does that stop any collection actions they might take?

Requesting more time usually pauses collection actions while your case is being reviewed, but it's not guaranteed. Make sure you get confirmation (ask for a transaction ID or confirmation number) when you request the extension. The safest approach is to send a written response by certified mail before the deadline stating that you're disputing the amount and gathering documentation to support your position. This officially stops the collections process while your case is reviewed. Then follow up with your complete documentation once you have everything organized.

If the error was the IRS's fault, you can request interest abatement using Form 843. I did this last year after they misapplied a payment, and they approved it and removed all the interest charges. Make sure you clearly explain how the error was caused by the IRS and not by anything you did.