15 How do you calculate how much to pay for estimated taxes? Is there some formula or percentage I should be setting aside from each payment I receive?

10 The safe harbor method is to pay either 90% of your current year's tax liability or 100% of last year's tax liability (110% if your income is above $150,000), whichever is lower. For a quick practical approach, I set aside about 30% of all my 1099 income - roughly 15% for self-employment tax and 15% for income tax. This has worked well for me, but your tax bracket might differ. The IRS has Form 1040-ES with a worksheet to calculate more precisely, or you can use tax software that offers quarterly tax calculators.

4 Does that apply even if you're just a freelancer/contractor working for one company? I thought B&O tax was just for actual businesses with multiple clients.

Good point about the improvements! For the first house, I actually did replace the roof ($14k) and installed a new HVAC system ($9k). Would I need receipts for all of these improvements or are there other ways to document these if I can't find all the paperwork?

Receipts are definitely the best documentation, but if you don't have them all, there are other options. Bank or credit card statements showing payments to contractors can work. Even emails confirming quotes that you accepted can help establish the costs. For major improvements like a roof or HVAC system, you might also have permit records with your local building department that can verify the work was done. Some contractors might also have records they can provide if you reach out to them. The IRS knows people don't always keep perfect records, but they do expect you to make a reasonable effort to document these costs.

Not necessarily. The test is whether you lived in it as your primary residence for 2 of the 5 years before selling. Who lives in it during other periods doesn't affect that qualification. If OP had rented it out, there might be some depreciation recapture to deal with, but since no rent was collected, that's not an issue.

That's a really important distinction. How can you tell if your LLC is being taxed as an S-Corp vs a disregarded entity? I filed paperwork when I started my business but honestly don't remember what I selected.

You can tell by looking at what tax forms you've filed in the past. If you've been filing Schedule C with your personal tax return, then your LLC is being treated as a disregarded entity. If you've been filing Form 1120-S and receiving a K-1 from your business, then you elected S-Corp treatment. If you're still unsure, you should be able to check with the IRS. You would have filed Form 2553 to elect S-Corp status. If you never filed that form, then you're most likely a disregarded entity by default. This distinction is crucial for understanding how losses flow through to your personal taxes.

Yes, the rules definitely changed. Starting with tax years after 2020, NOLs can only be carried forward (not back, except for some farming losses). Also, you can only use the NOL to offset up to 80% of your taxable income in any future year. So if you made $10,000 this year, you could only use $8,000 of your NOL, and would have to carry the rest to future years.

Thanks for explaining that! That makes sense why TurboTax was limiting how much I could claim. So I'll have to carry forward part of my loss to next year too. Wish they'd make these tax rules simpler to understand.

Do you know if there are different thresholds for married filing jointly people who live abroad? My wife and I are US citizens but we've been living in Germany for the past 5 years.

Yes! For married filing jointly taxpayers living abroad, the thresholds are even higher - $400,000 at year-end or $600,000 at any point during the year. So if you and your wife are under those thresholds, you wouldn't need to file Form 8938. Just be sure you still consider FBAR requirements (FinCEN Form 114) which has a separate $10,000 threshold regardless of where you live. Those are often confused but are two separate filing requirements.

Tell me about it! I pay my accountant $1,200 every year just to file these foreign asset forms, and I've never owed a penny of additional US tax on them. The penalties are so ridiculously disproportionate too - $10,000 for a paperwork error on accounts where you've paid all taxes due? It's just revenue generation at this point.

I had no idea this was even a thing! Do you know if there's a specific form I need to fill out to request this? And does it matter if I've already set up a payment plan?

You don't need a specific form - you can request it by phone when you call the IRS. Just specifically ask for "first-time penalty abatement" and explain that you've had a good compliance history. They'll check if you qualify right on the call. It doesn't matter if you've already set up a payment plan - you can still request the abatement. The payment plan is for the total amount, but if they approve your abatement request, they'll reduce the total and adjust your payments accordingly. Be aware this only removes penalties, not interest or the actual tax owed, but it can still save you a decent amount.

Do you just use the calculator on the IRS website? I've tried that before and found it super confusing with all the questions about dependents and deductions.