I tried the Vanguard one but got confused by some of the terminology they use. Does anyone know if the SE income they ask for is before or after business expenses? And do these calculators account for that reduction factor people mentioned above?

The SE income they ask for is your net profit from Schedule C - so that's after all your business expenses. And yes, both Vanguard and Fidelity's calculators do account for the reduction factor - they're calculating the actual 25% of your compensation after adjustments, not the simplified 20% rule of thumb. Most people get confused because the true formula is a bit circular (since your contribution impacts the base it's calculated on), but these big financial institutions have accurate calculators. Just make sure you're entering your net profit from self-employment, not your gross receipts!

Could you maybe explain how the circular calculation actually works? I've been trying to understand it but getting confused. Is it because the SEP contribution itself reduces the income that the 25% is based on?

Would we calculate those quarterly payments just based on our investment income or would we need to factor in possible underwithholding from our regular jobs too? And is there some calculator to figure out how much to send each quarter?

You'd want to account for both the investment income and any potential underwithholding from your jobs. The simplest approach is to take what you owed this year (your $4,300) and divide by 4 - that would be roughly $1,075 per quarter. That's assuming your income situation stays similar. There's actually a worksheet in the Form 1040-ES instructions that helps you calculate exactly what you should pay. Alternatively, if you pay at least 100% of last year's tax liability (or 110% if your AGI is over $150,000), you're generally safe from underpayment penalties even if you end up owing more when you file.

This is such a good point! My company withholds exactly 22% from bonuses regardless of my W-4 settings, and it's never enough. I always have to request additional withholding when I get my annual bonus.

I hadn't thought about the tax implications for the sellers. Good point about finding a middle ground - maybe I can present both options to them and see which they prefer. What would be considered a reasonable balance? Like maybe 50/50 split between higher principal/lower interest vs. lower principal/higher interest?

There's no exact formula for the "perfect" balance, but I'd approach it by starting with market-rate interest for this type of seller financing (probably in the 8-12% range currently) and then calculate what that would look like over your loan term. From there, you could model a slightly higher interest rate (maybe 1-2% above market) and show the sellers both scenarios. The key is making sure whatever you decide can be defended as commercially reasonable if questioned. The sellers might actually prefer a slightly lower total payment amount with more characterized as principal rather than a higher total with more as interest, so be prepared to show them the after-tax impact of different structures.

This is really important! I did an asset purchase for my business and got to write off way more than I would have with a stock purchase. The seller wanted stock sale for their tax benefits but we negotiated on price instead.

The Taxpayer Advocate Service sounds interesting - do you know how long it typically takes to get help from them? And would they be able to help with e-filing specifically or just general tax issues?

The Taxpayer Advocate Service typically takes 2-4 weeks to get assigned to your case, but they're absolutely able to help with e-filing issues, especially when there are technical barriers preventing you from filing correctly. They're particularly helpful in situations like yours where you're actively trying to comply with tax obligations but facing system limitations. For faster assistance, I'd recommend trying the solutions others mentioned first (different software or calling the IRS directly). The Taxpayer Advocate is great as a backup option if those routes don't work out. They can sometimes expedite processing of paper-filed amended returns in cases where e-filing isn't possible.

This is the correct answer! The IRS systems require a value for prior year AGI even if you didn't file. Using $0 is the standard workaround.

This is such an important distinction! I messed this up one year and it was a nightmare to fix. Quick question - if you have access to both an HSA and FSA (limited purpose FSA), can you contribute to both in the same year? My benefits coordinator gave me conflicting info.

Yes, you can contribute to both an HSA and a Limited Purpose FSA in the same year. The key is that it must be a "Limited Purpose" FSA that only covers dental and vision expenses, not a regular medical FSA that covers all healthcare expenses. Regular medical FSAs would make you ineligible for HSA contributions, but the Limited Purpose FSAs are specifically designed to work alongside HSAs. This combination actually gives you the most tax advantages, as you can use the Limited Purpose FSA for immediate dental/vision needs while letting your HSA investments grow for future medical expenses.

The limits for 2024 are higher just fyi: - $4,150 for individual coverage - $8,300 for family coverage Plus still the +$1,000 for 55+ folks

Is the contribution limit per calendar year or plan year? My company's health plan runs July-June but taxes are Jan-Dec. Always confuses me when figuring the max I can contribute.