I went through this exact same situation last year with my dog walking side business! The good news is TurboTax makes it pretty straightforward once you know the steps. When you get to the business income section, you'll enter your 1099-K information using your SSN as the tax ID. TurboTax will automatically generate Schedule C for your self-employment income. The key thing is to make sure you enter the gross amount from Box 1a of your 1099-K - that's what Square reported to the IRS. One thing that really helped me was keeping a simple spreadsheet throughout the year tracking all my business expenses. Beyond the Square processing fees, don't forget about: - Hair styling tools and equipment - Products you use on clients - Any licensing or certification costs - Transportation to client locations - Even a portion of your home wifi if you use it to manage bookings Also be prepared for the self-employment tax hit - that caught me off guard my first year. You'll owe both regular income tax plus the additional 15.3% for Social Security and Medicare on your net profit. Setting aside about 25-30% of your side business income throughout the year helps avoid a big surprise at tax time. The most important thing is just being honest and thorough with your reporting. The IRS isn't trying to trick you - they just want to make sure the income matches what was reported by Square.

Just wanted to add something important that hasn't been mentioned yet - make sure you're keeping detailed records of ALL your cash transactions too, not just what shows up on the 1099-K! The 1099-K from Square only reports your electronic payments, but if you're doing haircuts and styling, you probably also receive cash tips or some clients might pay cash directly. The IRS expects you to report ALL your income, not just what's on the 1099-K form. I learned this the hard way when I got audited for my massage therapy side business. Even though my 1099-K showed most of my income, the auditor asked for records of any cash payments too. Now I keep a simple log of every service I provide, whether paid by card through Square or cash. Also, since you mentioned you didn't set up the tax settings correctly in Square, you'll want to be extra careful about sales tax if your state requires it for personal services. Some states exempt personal services like haircuts from sales tax, but others don't. You might need to file separate sales tax returns depending on your location. TurboTax won't help with state sales tax obligations - that's usually handled through your state's department of revenue. Worth looking into before you file your income taxes!

I went through this exact same situation with my daughter when she turned 18 and started college! You're absolutely right that you can claim her as your dependent while she files her own return - this is actually a really common arrangement for college students with part-time jobs. Based on what you've described, you clearly meet all the requirements for claiming her as a qualifying child: she's under 24, a full-time student, lives with you more than half the year (college counts as temporary absence), and most importantly - you're providing way more than half her support. When you're covering tuition, housing, food, medical insurance, phone, and other major expenses while she only makes $800-900/month, the math is pretty straightforward. Here's how it works: Your daughter files her own return for her mall job income and makes sure to check the box that says "Someone can claim you as a dependent." She'll still get back most of what was withheld from her paychecks as a refund. You claim her as your dependent on your return and can take advantage of education tax credits like the American Opportunity Credit, which can save you up to $2,500. One important tip - have your daughter review her W-4 at work to make sure her withholding is set up correctly as a dependent. This helps avoid any surprise tax bills at the end of the year. Most employers are very familiar with helping student employees get this right. It really is a win-win situation when done properly - you both benefit financially and everything stays above board with the IRS!

This is such a helpful thread! I'm in a very similar situation with my 18-year-old who just started college and has a part-time job at a local bookstore. Reading through everyone's experiences has really clarified things for me. One thing I wanted to add that I learned from our tax preparer - if your daughter has any 1098-T forms from her college showing tuition payments, make sure to keep those organized. Since you're claiming her as a dependent and paying for her education expenses, you'll need those forms to claim the American Opportunity Credit. Also, I discovered that even though my daughter's scholarship covers part of her tuition, I can still claim the education credit for the portion I pay out of pocket. The scholarship money doesn't count against the support test either, which was a relief since I was worried it might complicate things. Thanks to everyone who shared their experiences - it's so reassuring to know this is a common situation that many families navigate successfully!

Just a heads up - make sure you're looking at your actual W-2 to confirm the ESPP discount is really included there. Some companies handle this differently! My company actually doesn't include the ESPP discount in the W-2 for disqualifying dispositions - instead they report it on a separate 3922 form and I have to report it as "Other Income" when I file. Worth double-checking how your specific company handles it so you don't make incorrect adjustments.

This thread has been incredibly helpful! I'm dealing with a similar ESPP situation and was totally confused about the basis adjustments. One thing I'd add for anyone else reading this - if you have multiple ESPP purchases throughout the year at different discount rates, make sure you're tracking the specific discount amount for each lot separately. My company's supplemental statement breaks this down by purchase date, which is crucial since the 15% discount applies to different FMV amounts depending on when you bought. Also, don't forget that if you had any dividend reinvestments on your ESPP shares before selling, those might affect your basis calculation too. I almost missed that detail until I noticed some small amounts on my brokerage statement. Thanks everyone for sharing your experiences - this stuff is way more complex than it should be!

Does anyone know if you actually NEED to make this election for small rental property repairs? I've been reading that if all your repair expenses are under $2,500 per invoice, you might qualify to deduct them outright as repairs without making this formal election. I'm using Cash App Taxes too and can't figure out where to put this election statement, so I'm wondering if I can just skip it and still deduct my minor expenses.

I actually had this exact same issue with Cash App Taxes last year! After trying multiple approaches, I found the solution in an unexpected place. Go to your Schedule E section, select the specific rental property you're working on, then look for a section called "Property Details" or "Additional Property Information." Within that section, there should be a text field for "Notes" or "Comments" - it's usually near the bottom and easy to miss. I put my de minimis safe harbor election statement there using this language: "Taxpayer elects the de minimis safe harbor under Treasury Regulation Section 1.263(a)-3(h) for all eligible expenditures for the tax year ending December 31, 2024." My return was accepted without any issues, and I've used this same approach for two years now. The key is that the election needs to be associated with your rental property reporting, which Schedule E accomplishes perfectly. If you still can't find that field, try updating Cash App Taxes - they've moved some sections around in recent updates. Hope this helps!

This whole thread has been eye-opening! I had no idea FreeTaxUSA offered electronic document attachments - that's exactly what I've been looking for. I've been using TurboTax for years and got so frustrated with their constant upselling and the mail-in requirement for investment documents. A couple of questions for those who have made the switch: 1. How does FreeTaxUSA handle imported data from brokers? Does it import cleaner than TurboTax or do you still need to do manual cleanup? 2. For the electronic attachments, do you typically scan physical documents or can you usually download PDFs directly from your brokerage accounts? I'm definitely planning to try FreeTaxUSA next year. Between the free federal filing and electronic attachments, it sounds like it could save me both money and a lot of hassle. Thanks everyone for sharing your experiences!

I've been following this discussion and wanted to add my experience for anyone still on the fence about switching from TurboTax to FreeTaxUSA. I made the switch three years ago after getting hit with multiple upgrade fees in TurboTax (first for having investment income, then another fee for needing to attach documents). The breaking point was when I had to mail my 1099B supporting docs and they got lost in transit - took months to resolve with the IRS. FreeTaxUSA's electronic attachment feature has been a lifesaver. I typically attach: - All 1099B statements from my brokers - Any adjusted cost basis calculations I've done manually - Sometimes a brief explanation letter if I have unusual circumstances The 15MB limit mentioned earlier is generous for most situations. I've never hit it even with documents from 4 different brokers. The key is using PDF compression if your files are large. One thing I haven't seen mentioned yet - FreeTaxUSA also lets you save your return as a draft and come back to it later, which is helpful when you're gathering documents from multiple sources. You can upload attachments as you go rather than having to have everything ready at once. The cost savings alone (easily $100+ per year) make it worth switching, but the convenience of electronic filing with full documentation attached is what keeps me using it.