Another schedule C question - Does anyone know if TurboTax handles this "at risk" question automatically? I'm trying to decide which tax software to use for my freelance work.

I went through this same confusion last year! The "at risk" question is basically asking whether you could personally lose the money you invested in your business. For your photography business, since you spent $3,500 of your own money on equipment and software, that investment is "at risk" - if your business fails, you lose that money. You'd select "all investments are at risk." The "some investments not at risk" option is for very specific situations like non-recourse loans (where you can't be held personally liable beyond specific collateral) or certain complex partnership arrangements. These are pretty rare for solo freelancers. Don't overthink it - as a sole proprietor who invested your own cash, you're almost certainly in the "all investments at risk" category. The IRS language makes it sound scarier than it actually is!

I'm an owner-operator and just wanted to add that this confusion is super common. Like half the guys at my terminal are doing their taxes wrong. Remember: - The TRUCK (asset) = depreciable - The INTEREST on loan = deductible expense - The PRINCIPAL on loan = NOT deductible (that's what depreciation covers) - REPAIRS/MAINTENANCE = always deductible The IRS isn't dumb - they know what a loan payment includes and they'll catch double-dipping eventually!

This is exactly why I love this community - so much good info here! I've been an owner-operator for 3 years and STILL learn something new about taxes every season. Just to add another perspective: if you're ever unsure about your specific situation, definitely keep detailed records of everything. I scan all my loan statements, receipts, and maintenance records into a folder on my phone throughout the year. When tax time comes, I can easily separate the interest payments from principal and have backup for any deductions. Also worth mentioning - if you're doing major repairs vs improvements on your truck, those have different tax treatments too. Regular maintenance and repairs are fully deductible in the year you pay them, but improvements that extend the truck's life or increase its value might need to be depreciated separately. The tax code for trucking can get pretty complex!

Quick tip - if your combined mortgage debt (primary mortgage + HELOC) is over $750,000, you might hit the cap on deductible interest. Worth checking with a tax professional if you're in that situation. I also found my credit union didn't automatically send a 1098 for my HELOC when the interest was under $600, but they did provide a year-end statement showing the interest paid. The IRS still let me claim it with that documentation.

Just wanted to add my experience for anyone else in a similar situation. I took out a HELOC last year specifically for home improvements and was able to deduct 100% of the interest since I used every penny for qualifying renovations (new HVAC system, flooring, and electrical upgrades). One thing I wish I'd known earlier - make sure you have a clear paper trail from the HELOC draws to the home improvement expenses. I kept a spreadsheet tracking each draw amount, date, and what specific project it funded, along with all contractor invoices and receipts. This made tax filing much smoother and gives me confidence if the IRS ever questions the deduction. Also, even though my lender didn't send a 1098 (interest was only about $400 for the year), I was still able to claim the full deduction using my year-end loan statement. The key is just having proper documentation of both the interest paid and how the funds were used.

I've been through this frustrating situation twice, and here's what I learned that might help you get answers faster. First, don't wait - call the IRS at 800-829-1954 as soon as possible given your urgent need for your mom's medical supplies. The transcript updates for returned checks are notoriously unreliable and can lag weeks behind reality. When you call, ask specifically for them to run a "refund trace" - this gives you more detailed information than just asking if the check was returned. Also, have your exact filing address ready and compare it word-for-word with what's on your actual mailbox. I discovered my check was returned because I used "Street" instead of "St" on my return. If there is an address discrepancy, they can often reissue the check immediately during the call and provide you with a new timeline. The hold times are awful (I waited 2.5 hours last time), but it's infinitely better than waiting weeks for a transcript that may never update. Given the medical urgency, this is definitely worth the phone hassle rather than relying on the automated systems.

I'm dealing with a very similar situation right now - my refund was supposedly mailed 12 days ago and still nothing showing up. After reading through everyone's experiences here, it's becoming clear that waiting for transcript updates is basically pointless when you need urgent answers. The fact that so many people have confirmed the transcript system can lag weeks or never update at all for returned checks is really concerning. Given your urgent need for your mom's medical supplies, I'd definitely echo what others have said about calling immediately. The "refund trace" suggestion from @38b8497ad8b0 sounds like the most direct approach to get real answers. I'm planning to call tomorrow myself and specifically ask for that rather than just general refund status questions. It's frustrating that we have to go through phone hell to get basic information about our own money, but it seems like that's the only reliable path forward. Hope you get this resolved quickly - medical expenses can't wait for the IRS's slow systems to catch up.

Has anyone used TurboTax to report a business sale? I'm trying to figure out if the self-employed version can handle this or if I need to upgrade to their business version?

I just went through this exact same situation when I sold my consulting firm last year. The key thing that helped me was understanding that you need to treat this as an asset sale, not a stock sale, which means each component of your business gets reported differently. For your client list and goodwill (the intangible value you built up over 8 years), these qualify as Section 197 intangibles and should be reported on Form 4797 Part I since you held them for more than a year. This gives you long-term capital gains treatment, which is much better than ordinary income rates. The installment sale aspect is important too - you'll definitely need Form 6252 to report the payments you'll receive over the next two years. This lets you spread out the tax liability rather than paying it all upfront on the 70% you received. One thing that caught me off guard was Form 8594 (Asset Acquisition Statement) - both you and the buyer need to file this with consistent asset allocations. Make sure your purchase agreement specifies how the sale price is allocated across different asset categories, or you might run into issues later. I'd strongly recommend getting professional help for this if you can. The classification of assets can make a huge difference in your tax bill, and there are specific rules about what qualifies for capital gains vs ordinary income treatment that aren't always intuitive.