Has anyone tried using a payment app like Venmo or Cash App for these private seller transactions? I'm wondering if the digital receipt from that would be sufficient documentation.

Great question! As someone who's been running a small carpentry business for 3 years, I can share what's worked for me. You definitely need documentation for all business expenses, even from private sellers. Here's my system: I created a simple receipt template on my phone that I fill out on the spot. It includes: seller name, contact info, date, detailed description of materials (species, dimensions, quantity), purchase price, and payment method. I have the seller sign it if they're willing, take a photo of the materials, and note the intended business use. For sellers who won't sign anything, I still document everything I can and take timestamped photos. I also photograph my cash withdrawal receipt if I paid cash, which creates a paper trail. The IRS wants to see that you have adequate records to substantiate your business expenses. Consistency is key - use the same documentation method every time. I keep all my receipts (both formal and self-created) organized by month in both physical and digital folders. One tip: if you're buying expensive specialty wood, consider bringing a witness who can verify the transaction if the seller is hesitant about paperwork. This has helped me a few times with valuable hardwood purchases from estate sales.

Don't forget about the Qualified Business Income deduction (Section 199A)! As a self-employed rideshare driver, you can potentially deduct 20% of your net business income. This is ON TOP OF your regular business deductions like mileage or car expenses. Also, make sure you're setting aside money for self-employment taxes. The current rate is 15.3% of your net earnings (to cover Social Security and Medicare taxes that an employer would normally handle).

Something NOBODY mentioned yet - if you're making decent money with rideshare, you should be making QUARTERLY estimated tax payments! I learned this the hard way and got hit with underpayment penalties. Since you don't have an employer withholding taxes, you're supposed to send estimated payments to the IRS four times a year. The due dates are April 15, June 15, September 15, and January 15 (of the following year).

Has anyone used any specific tax software that handles household employee situations well? I tried using [popular tax software] last year for my mother's caregiver and it was a nightmare trying to figure out the Schedule H and W-2 generation.

I went through this exact same situation with my grandmother's caregiver two years ago and learned some hard lessons. First, the IRS classification really does depend on the degree of control you have over the work, not just whether they work for other families. If you're directing what tasks need to be done, when they need to be at your home, and how the care should be provided, you're likely an employer regardless of their other clients. One thing I wish someone had told me earlier: even if you determine she should get a 1099-NEC as an independent contractor, you still need her Social Security Number or Individual Taxpayer Identification Number (ITIN), her full legal name, and address before you can file anything. The deadline for giving her the form is January 31st, and you need to file it with the IRS by the end of February (or March 31st if filing electronically). But honestly, given that you're paying her $26,000+ annually for regular ongoing care work in your home, this sounds like a textbook household employee situation to me. I'd strongly recommend getting professional help to sort this out properly - the penalties for misclassification can be significant, especially when you're dealing with this much money.

Has anyone used a tax professional to help with claiming these education credits retroactively? I'm in a similar situation trying to remember which credits I used years ago but I'm worried about making mistakes.

One thing to keep in mind about the Texas Tomorrow Fund - since it's a prepaid tuition plan, you'll want to check if your parents received a 1099-Q form for the distributions used to pay your tuition. This would show the amount that was distributed from the plan to cover your education expenses. If the entire tuition amount was covered by the prepaid plan and reported on a 1099-Q, then those expenses generally can't be used again for education tax credits. However, you might still be eligible for credits based on other qualified expenses you paid out of pocket, like mandatory fees, books, or required course materials. Also, don't forget that you can amend returns for up to 3 years after the original filing date (or 2 years after you paid the tax, whichever is later). So if you discover you were eligible for credits in 2014/15 that you didn't claim, you might still be able to file amended returns for those years if they're within the statute of limitations.

FYI - there's another situation where you need to file Schedule B regardless of the amount of interest or dividends: if you have any foreign accounts. I found this out the hard way after getting a notice from the IRS. Even if you only have $5 of interest total, if any of it came from a foreign bank account, you still need to file Schedule B and check that box in Part III.

Just wanted to add another important detail that I learned when I had to file Schedule B for the first time - you need to list ALL payers of interest and dividends on Schedule B, not just the ones that put you over the threshold. So even if you have 10 different accounts contributing small amounts that together exceed $1,500, you have to list every single payer on the form, including their name, address, and the amount they paid you. It can make for a pretty long form if you have accounts scattered across multiple banks and brokerages. The IRS uses this information for matching purposes - they want to see that what you're reporting matches up with all the 1099-INT and 1099-DIV forms they received about you. Missing even a small payer can trigger a notice later on.