That navigation path helped! So if I understand correctly, we need to find out what his step-mother originally paid for the property? The problem is she bought it like 30 years ago and we're not sure if she has records. Does TurboTax allow us to estimate, or will that cause problems?

Yes, ideally you would get the original purchase price from 30 years ago. If she doesn't have exact records, a reasonable estimate is allowed, but you should document how you arrived at that estimate in case of an audit. You could check county property records which might show the historical purchase price. Another approach is to look at similar properties in the area that sold around the same time she purchased it. If all else fails, you can use a conservative estimate based on local real estate historical data, but make sure to note how you determined the value. Remember, a higher basis means less taxable gain, but you need to be able to justify the number if questioned.

I used TaxAct last year for a 1099-S. In TaxAct, you need to go to the Federal section, then Income, then Investment Income, and there should be an option for "Sale of Home/Real Estate (Form 1099-S)". The interface is different from TurboTax but it asks for basically the same information. They have a search function at the top where you can just type "1099-S" and it should take you right to the correct section.

Do you think the $600 was worth the fee you paid to the tax pro? I'm wondering about the cost-benefit analysis. Also, now that you know about that credit, couldn't you just claim it yourself using software in future years?

Totally worth it - I paid $220 for the service, so I came out $380 ahead. And yes, now that I know about the credit, I can claim it myself going forward. I actually went back to software this year and made sure to look for that specific credit. I think seeing a pro once every few years as a "check-up" is a good strategy. Then you can self-file in between knowing you're doing it right. Tax laws also change pretty frequently, so it's good to get a professional review periodically.

Be careful with "free" filing! I tried that last year and as soon as I needed to file in two states they hit me with charges. Read the fine print - most of them only include ONE state for free.

Would they really go after someone for less than a pound in unpaid tax though? Seems like it would cost them more to send the letter than they'd get back.

It's not about the amount, it's about the principle. HMRC systems are increasingly automated and can pick up discrepancies between what platforms report and what you declare. My friend didn't get in serious trouble, but did have to file an amended return and pay a small penalty that was way more than the actual tax due. The real issue isn't the £2 over - it's that once you're over the allowance threshold, technically the full amount becomes declarable (though you still get to claim the £1000 allowance against it). HMRC might not chase 80p, but they might question why £1002 of income wasn't declared at all.

That's not correct. The £1000 trading allowance absolutely applies to self-employed work including Uber. Being self-employed doesn't change the allowance - that's precisely what the trading allowance is for: small amounts of self-employed/trading income.

My kids are 12 and 15, so they qualify for the Child Tax Credit. Would that really reduce my withholding to zero though? And yes, both employers use the new W-4 form (the one without allowances).

The Child Tax Credit could significantly reduce withholding but shouldn't take it all the way to zero, especially with your combined income. The credit is worth up to $2,000 per qualifying child, but that's spread across your entire tax year. With the new W-4 form, the issue is almost certainly that neither employer knows about your other job. When you earn $1,750 bi-weekly from one job, that's about $45,500 annually - and a single taxpayer with two dependents making that amount would have very little federal tax liability after standard deduction and child tax credits. Same with your second job at $54,600 annually. But when combined ($100,100), you're in a higher tax bracket and the calculations completely change. This is exactly why the W-4 has that multiple jobs section that needs to be completed.

This happened to my brother too. If you check that box on both forms, each employer thinks the other one is handling most of the withholding. It's counterintuitive but checking that box actually LOWERS the withholding from that job because it assumes withholding is happening elsewhere.

Oh this is a great point I hadn't even considered! I do arrange installation through subcontractors for about 60% of my projects. Would that still count as me providing installation services even though I'm subcontracting it out? Or does it matter that I'm including it as one bill to the client?

Generally what matters is how you present it to the client. If you're billing the client for a single transaction that includes both products and installation (even if subcontracted), most states will look at the entire transaction as a whole when determining tax treatment. If you separately state the charges on the invoice, some states will allow you to collect tax only on the product portion. But this varies dramatically by state. In some states like California, even separated charges might be considered part of a "bundled transaction" if they're part of the same project.

Yep, Colorado is especially bad with this! Almost 100 different local tax jurisdictions, many with their own rules. Louisiana is another nightmare state for local taxes. That's why I ended up using a sales tax compliance service rather than trying to figure it all out myself.