What about bank statements? Should I bring those too? I have most of my Amazon expense receipts saved but I'm not sure what else they might want to see related to my finances.

Yes, definitely bring your bank statements, especially ones showing your business expenses. The Revenue Officer will want to understand your complete financial picture. Bank statements help verify both your income sources and your expenses. Having those statements also helps with credibility - it shows you're being transparent and cooperative. Focus on the last 3 months at minimum, but if you have statements going back through the unfiled tax periods, those would be valuable to bring as well.

Valid point! I got a scam IRS letter once that looked super official. Real Revenue Officers will also have a badge and ID they can show you. And they never demand immediate payment during the first meeting.

4 Do you know if there's an easy way to get copies of old returns if you didn't save them? I can't find my 2022 return anywhere and I'm worried I'll need it.

21 You can request tax transcripts directly from the IRS website through their "Get Transcript" service. They offer several types, but what you'll want is the "Tax Return Transcript" which shows most of the line items from your original tax return, including your AGI. You can get these online immediately if you create an account on the IRS website, or request them by mail which takes about 5-10 business days. The online method requires more verification steps but gives you instant access. It's totally free either way and is the official solution for when you don't have copies of your previous returns.

6 I've used TaxAct for the past 3 years including one late filing. It handles penalties automatically and was way cheaper than TurboTax. The interface isn't as pretty but it gets the job done and has all the same features that matter.

So what about if there's a real business conference and I bring my kid who works for my business? Is any part of that deductible or is it all considered personal?

If there's a legitimate business conference and your child who legitimately works for your business has a valid business reason to attend, then their expenses related to the conference itself would be deductible as a business expense. This includes their registration, their portion of the hotel room during the conference dates, and their meals while attending business activities. However, if you extend the trip for sightseeing or vacation activities, those additional days would not be deductible. And any activities that are clearly personal in nature (like visiting tourist attractions or entertainment) wouldn't be deductible either, even during the business portion of the trip. The IRS looks at the primary purpose of each expense.

Your kids would only have to file taxes if their income exceeds the standard deduction (which is $13,850 for 2025). So if they make less than that, they typically don't have to file a federal return. But you still need to keep proper payroll records, issue them a W-2, and follow all employment laws.

Thanks for the warning! Did you have to do anything special to get it fixed when the payments stopped? Or just call the IRS? I'm definitely going to mark my calendar to check after each payment date now.

I had to call the IRS, which was a complete nightmare - took three days of trying before I got through. They claimed my bank had rejected the withdrawal (which wasn't true - my bank had no record of any attempt). They had to set up the whole payment plan again, and I had to pay an additional fee for the "reinstatement" even though it was their error. The most frustrating part was they had my current contact info but never tried to notify me until after I had technically defaulted. My advice is to check your bank account AND your IRS account online every month, and if you see any issues, deal with them immediately before they snowball.

Setting up an installment agreement before the filing deadline counts as meeting your obligation. The agreement itself is considered timely, even if the first payment comes later. There will still be some interest and smaller penalties, but you avoid the big failure-to-file penalty. It's like telling the IRS "I acknowledge I owe this and commit to paying on this schedule" rather than ignoring the debt. As long as you keep making the agreed payments, you're in compliance.

I'll definitely look for Form 3922! And good point about checking his paystubs - I hadn't thought to look there. Is there any specific section on the paystub where stock compensation typically appears? Also, if the matched shares are treated as RSUs, would that change how we calculate the basis?

Stock compensation usually appears as a separate line item on paystubs, often labeled something like "Stock Awards" or "Equity Compensation." Sometimes it's under a non-cash benefits section. Look at paystubs from periods immediately following grant dates, as that's when the income would typically be recognized. If the matched shares are treated as RSUs, the tax treatment is actually similar, but the timing might be different. With RSUs, the taxable event occurs at vesting, not at grant. The FMV at vesting becomes your basis, and any subsequent appreciation is capital gain. With matched ESPP shares, the taxable event is usually at grant. The documentation from your husband's company should clarify which approach they're using.

Section 83(b) elections are usually more relevant for restricted stock with vesting conditions, not immediate stock matches in an ESPP. From what OP described, it sounds like the matched shares are granted immediately without vesting requirements, so 83(b) probably wouldn't apply here.