I went to Jackson Hewitt once and never again. The "tax professional" was literally reading from a script and typing my answers into the same software I could use at home. When I asked about deducting home office expenses for my freelance work, they seemed confused and had to ask someone else. If u have a simple return, save ur money and DIY. If ur situation is complex like yours sounds, find a real CPA or EA (enrolled agent). National chains are basically just using the same software you can buy, but charging you $300+ for the privilege.

I went through something very similar last year - W-2 job until August, then multiple freelance clients with different 1099s, plus I moved states in July. I ended up going with Jackson Hewitt and honestly, it was worth it for the peace of mind. The key thing is what others mentioned - ask specifically for someone experienced with self-employment and multi-state returns. My preparer caught several deductions I never would have thought of, like the moving expense deduction (which is more limited now but still applies in some situations), partial business use of my car between freelance clients, and some startup costs for my freelance work. The multi-state part was especially tricky because I had to file as a part-year resident in both states, and there were some reciprocity rules I didn't understand. She walked me through everything and made sure I wasn't double-taxed on any income. I paid about $380 total for federal and two state returns with Schedule C. Yeah, it's pricey, but considering I would have probably screwed something up doing it myself and potentially faced penalties or missed deductions, I felt it was worth it. This year I might try one of the AI options people are mentioning though - seems like the technology has gotten a lot better.

Does anyone know if using the free version through IRS Free File means you don't get certain features? Like will it still do all the calculations and check for errors like the paid versions? I'm always nervous about making mistakes on my taxes.

This is really helpful timing! I just got my W-2 and was dreading the whole tax filing process. I've used TurboTax for years but the fees keep going up - paid almost $120 last year for federal and state filing plus some "premium" features I probably didn't even need. Quick question though - when you say AGI under $41,000, is that before or after standard deduction? I'm a teacher and my gross salary is around $43k, but after my 403(b) contributions and other pre-tax deductions, my taxable income is definitely under $41k. Want to make sure I understand the qualification correctly before I get started with FreeTaxUSA. Also appreciate all the discussion about the other tools mentioned here. Sounds like there are more resources available than I realized for making tax season less stressful!

Wait I'm confused... if a single-member LLC that's disregarded can't pay W-2 wages to its owner, when DOES it make sense to pay yourself a salary from your business? I've heard so many conflicting things about this.

This is a great discussion that highlights a really important distinction. I've seen this confusion come up repeatedly with small business owners who think paying themselves a W-2 salary will somehow legitimize their business or provide better tax benefits. The key takeaway here is that tax structure should follow legal structure, not personal preferences. A disregarded single-member LLC cannot create an employer-employee relationship with itself - it's legally impossible. Your friend's reasoning that it "feels more like a real business" doesn't change the fundamental tax law. Beyond the compliance issues everyone's mentioned, there are practical problems too. If your friend is filing employment tax returns (940, 941) for these phantom wages, he's creating a paper trail that doesn't match his actual business structure. This inconsistency is exactly what can trigger IRS scrutiny. The irony is that if he wants the benefits of paying himself a salary (like potential self-employment tax savings), he should consider making an S-Corp election. Then he'd be legally required to pay himself reasonable compensation as a W-2 employee, and any additional profits could be distributed without self-employment tax. But that's a completely different tax structure with its own requirements and limitations. Bottom line: work with the structure you have, not against it.

5 Did your brother get a mortgage to buy you out or did he pay cash? Just wondering because when I went through this with my family, my sister needed a mortgage and the bank required a formal appraisal, which then really helped with documenting the stepped-up basis for tax purposes.

I'm dealing with a very similar situation right now - inherited my mom's house with my siblings and had to figure out the tax implications when we sold it. The stepped-up basis rule that others mentioned is absolutely correct and will likely save you from owing much (if any) tax on this. One thing I'd add is to keep really good records of everything - the informal appraisal, any expenses related to the sale or transfer, and documentation of when your father passed away. Even if your brother's real estate agent friend just gave a verbal estimate, try to get that in writing if possible. Also, don't forget that you might be able to deduct certain expenses from the sale that could reduce any potential gain even further - things like legal fees, transfer taxes, or other costs associated with the property transfer between siblings. These can add up and further reduce your tax liability. The IRS is generally pretty reasonable about inherited property situations as long as you can show you made a good faith effort to determine fair market value at the time of death.

Great question! I just went through this exact situation last year. The tax bracket fear is totally overblown - you'll never make less money by earning more due to how progressive taxation works. One thing I'd add to the excellent advice already given: consider using the IRS Multiple Jobs Worksheet that comes with Form W-4. It's specifically designed for your situation and will tell you exactly how much extra to withhold. I found it more accurate than online calculators because it accounts for your specific filing status and deductions. Also, don't forget that retail jobs sometimes offer employee discounts which can add to your savings. At $17/hr for 15 hours weekly, you're looking at roughly $13,260 annually before taxes - even after proper withholding, that's still a significant boost toward your debt payoff goals. Just make sure you're prepared for the schedule demands everyone mentioned!

One thing I haven't seen mentioned yet is the timing aspect of starting your second job. Since we're already into 2025, you'll want to be extra careful about your withholding calculations because you'll have fewer pay periods to spread the additional tax burden across. I'd strongly recommend using the IRS Tax Withholding Estimator (irs.gov/W4App) rather than just the paper worksheet, since it can account for the partial year of second job income. When you input your information, make sure to include what you've already earned and had withheld so far this year from your main job. Also, consider this: at $58k + potential $12k from the retail job, you're looking at about $70k total income. That keeps you comfortably in the 22% bracket for 2025 (which doesn't kick in until around $47k for single filers). The real benefit is that extra $1000/month could knock out your credit card debt much faster, saving you tons in interest charges that far outweigh any additional tax burden. One practical tip: ask your retail employer about their payroll schedule. If they pay weekly while your main job pays bi-weekly, it might actually help smooth out your cash flow for debt payments!