What about Credit Karma Tax? I heard that's completely free even for more complicated returns. Has anyone tried it?

Credit Karma Tax (now called Cash App Taxes) is completely free and handles most tax situations well. I've used it for returns with some investments and a side gig. The interface is clean and it covers most forms. The only downsides: it doesn't support multiple state returns, certain less common situations (like foreign income), and doesn't offer as much guidance as paid options. If your return is moderately complex but doesn't have those specific issues, it's an excellent free choice. Just be aware they make money by recommending financial products to you based on your tax info - that's the tradeoff for the free service.

Just want to add that if your income is below $60,000 you might qualify for free in-person help through VITA (Volunteer Income Tax Assistance). They're IRS-certified volunteers who will prepare your return for free. Google "VITA tax help near me" to find locations.

I've heard you can deduct mileage for driving to job sites, but what if the work was at multiple houses in the same neighborhood? Do I track each trip separately or can I just estimate the total miles for all the jobs?

You need to track each trip separately for proper documentation. Keep a mileage log (there are free apps for this) showing the date, starting location, ending location, miles driven, and purpose of each trip. For multiple houses in the same neighborhood, each location is a separate job site. So if you drive from home to House A, then to House B, then back home, you'd record three legs: home to A, A to B, and B to home. The total mileage is deductible as long as each trip has a business purpose. Many people miss out on this valuable deduction because they don't keep good records, but it can really add up!

Your brother is giving you terrible advice that could get you in trouble. ALL income legally needs to be reported. The IRS has gotten much better at finding unreported income through bank deposit analysis and other means.

That's a really good point about unemployment. Do you know if I need to do anything special for the state tax situation? Like should I be filling out any specific forms now, or is that just something I handle when filing next year?

For the state tax situation, you don't need to do anything special right now other than making sure your employer knows you're a Wisconsin resident. When they set up your payroll, they should withhold Colorado state taxes since that's where you're working. When tax filing time comes, you'll file a resident return for Wisconsin (reporting all your income from all states) and a non-resident return for Colorado (reporting only the income earned in Colorado). Wisconsin will give you a credit for taxes paid to Colorado to avoid double taxation. Each state has different forms for this, but any decent tax software will walk you through it.

Not OP but I've dealt with this. You can maintain residency in one state while working temporarily in another. Maybe OP still has their permanent address, driver's license, voter registration, etc. in Wisconsin but is working in Colorado for a limited time. Residency definitions vary by state, but usually involve where you intend to make your permanent home.

Thanks for pointing this out! I'm not sure how my policy works tax-wise. It was through my employer but I think I did pay some portion of the premiums each month before I went on disability. How would I figure out if I paid with pre-tax or after-tax dollars?

You can determine this by looking at your last paystub before going on disability. Look for the disability insurance premium deduction and check if it's listed under pre-tax or post-tax deductions. If you don't have your paystubs, contact your HR department or benefits administrator - they can tell you exactly how your premiums were structured. If you paid even a portion of the premiums with after-tax dollars, then a corresponding percentage of your benefits would be non-taxable. For example, if you paid 40% of the premium with after-tax money, then 40% of your benefits would be tax-free.

They sent me a 1099-R that shows the full amount in Box 1, and it looks like it has a code in Box 7. Not sure what that means though.

The code in Box 7 of your 1099-R is super important! It tells you how the distribution is being characterized. For disability payments: Code 3 typically means disability payments before minimum retirement age - these are usually taxed as regular income. Code 7 is for normal distributions, sometimes used for disability after reaching minimum retirement age. If there's a value in Box 5 (Employee Contributions/Designated Roth Contributions), that's the portion that ISN'T taxable because you already paid tax on it!

Wow, $475 is so much more reasonable! Do you have any tips for finding someone good at that price point? Did you just Google local accountants or was it word of mouth? I'm definitely going to shop around this year.

I found my accountant through a local small business networking group in my area. Word of mouth referrals are gold for finding good accountants at reasonable rates. Check if there's a Chamber of Commerce small business group or even Facebook groups for local business owners in your area - then ask for recommendations. When interviewing potential accountants, ask specifically about their experience with pet service businesses or similar industries. Mine already had several dog walkers and pet sitters as clients, so she knew exactly which deductions to look for. Also ask about their communication style and availability throughout the year, not just at tax time.

I tried that route first and missed a bunch of deductions. Ended up hiring a pro who saved me way more than his fee. Software is fine if your business is super simple but it doesn't replace experience.