Nobody has mentioned Credit Karma Tax (now called Cash App Taxes) which is completely free for federal AND state! I switched from TurboTax 3 years ago and have saved hundreds. It handles W-2s and basic 1099 income no problem. The IRS direct file is only available in 12 states right now for the 2025 filing season as part of their pilot program. Unless you're in Arizona, California, Florida, Massachusetts, Nevada, New Hampshire, New York, South Dakota, Tennessee, Texas, Washington, or Wyoming, you can't use it yet.

Based on your situation (W-2 plus under $3,000 in side gig income), I'd definitely recommend FreeTaxUSA over filing directly through IRS.gov. The IRS website doesn't actually have comprehensive tax prep software - they mainly offer Free File Fillable Forms which are basically digital versions of paper forms without much guidance. FreeTaxUSA will walk you through everything step-by-step and handle your side gig income properly with Schedule C forms. Federal filing is completely free and it's much more user-friendly than trying to navigate tax forms on your own. Plus, you'll avoid the constant upselling that made you want to ditch TurboTax in the first place. The new IRS Direct File program everyone's talking about is still very limited - only available in 12 pilot states and doesn't handle all tax situations yet. For your second year filing with a straightforward but not completely simple situation, FreeTaxUSA hits that sweet spot of being comprehensive without being overwhelming.

Just wanted to add another perspective - I used to process dealer incentive payments for a major RV manufacturer. If your husband calls the manufacturer's dealer relations department (not just general customer service), they can usually look up payments by dealership and salesperson. They absolutely have records of every spiff paid out. Have him ask for the "dealer incentives coordinator" or similar title. They field these calls all the time!

As someone who works in tax preparation, I'd strongly recommend NOT filing without that expected 1099. Here's why: if the IRS receives a 1099 for $2500 that you didn't report, they'll send you a CP2000 notice (basically a bill for the unreported income plus penalties and interest). This usually happens 12-18 months after filing, and by then you could owe significantly more than the original tax due. Since 1099s were due January 31st, I'd give it until mid-February max before filing. In the meantime, have your husband contact his sales manager - they often have records of which manufacturers paid spiffs to which salespeople, even if they don't process the payments directly. Also check if his dealership uses any centralized payment systems like ADP or similar that might consolidate these payments. If you absolutely can't find the source by filing deadline, you can estimate the income and report it as "Other Income" on Form 1040. Better to overestimate slightly than underestimate and face penalties later.

I think people often confuse tax RESIDENCY rules (for income tax filing purposes) with Social Security/Medicare tax obligations. They're governed by different sections of the tax code! Even some tax preparers get this wrong. I've seen software engineers on EADs mistakenly told they're exempt when they're not. Always check IRS Publication 519 "U.S. Tax Guide for Aliens" - it covers this topic specifically.

Great thread with lots of helpful info! I just wanted to add that if you're unsure about your specific situation, you can also check Box 3 (Social security wages) and Box 5 (Medicare wages) on your most recent pay stub or W-2. If your employer is withholding these taxes, those boxes should show your wages subject to these taxes. Also, once you do get your actual Green Card, nothing changes regarding FICA taxes - you'll continue paying Social Security and Medicare taxes just like you are now with your EAD. The transition is seamless from a payroll tax perspective. One more tip: keep good records of all your Social Security contributions during your EAD period. When you eventually apply for Social Security benefits (whether retirement, disability, etc.), all these contributions will count toward your benefit calculation, regardless of whether they were made before or after you got your Green Card.

As someone who's been doing freelance digital art for about 3 years now, I can definitely relate to the tax confusion when starting out! You're asking all the right questions. One thing I wish I'd known earlier - keep track of your business expenses from day one, even small ones. I missed out on deducting things like PayPal fees, bank transfer fees, and even the cost of business cards or promotional materials in my first year because I didn't realize they counted. Also, since you mentioned you're keeping good records with spreadsheets, make sure you're also tracking your expenses in the same detail. I use separate columns for income source, expense category, and business percentage (like if I use my phone 30% for business vs personal). This makes Schedule C so much easier to fill out. For the quarterly payments, don't stress too much about the ones you've missed - the penalties are usually pretty small for first-time filers, especially if you're not making huge amounts yet. Just try to get current with the next payment and you'll be fine. The IRS also has a really helpful Publication 334 (Tax Guide for Small Business) that covers a lot of the self-employment basics if you want to read up on the details yourself.

One thing that really helped me when I started freelancing as a digital artist was setting up a separate business bank account, even though it's not required for sole proprietors. It makes tracking income and expenses so much cleaner, especially when tax time comes around. Since you mentioned you're making decent money ($4,200 in 6 months), you're definitely going to want to stay on top of those quarterly payments going forward. I'd suggest calculating what you think you'll make for the full year and then divide that by 4 for your remaining quarterly payments. Better to overpay slightly than get hit with penalties. Also, don't forget about state taxes if your state has income tax. Even though you mentioned your state doesn't charge sales tax on digital products, you'll still likely need to report your freelance income on your state return too. Each state handles this differently, so it's worth looking into your specific state's requirements for self-employment income. The good news is that once you get through your first year and understand the process, it becomes much more routine. You're already ahead of the game by keeping good records and asking these questions early!

Just fyi my accountant told me the income limit for qualifying relatives for 2025 filing season is actually $4,850 not $4,700 like someone said above. the numbers go up a little each year. but still sounds like your mil makes too much to qualify at $135/week.

I went through something very similar with my grandmother last year. The key thing that tripped me up was understanding that ANY money you give her counts as income, even if it's just a "thank you" or help with expenses. What ended up working for us was keeping the cash payments under $93/week (which keeps her under the $4,850 annual limit for 2025) and then covering more of her direct expenses instead. So instead of giving her extra cash, we started paying for things like her prescriptions, clothing, personal care items, and even set up a small monthly allowance on a prepaid card for incidentals. We were able to claim her as a dependent and got a nice tax break. The documentation was key though - we kept receipts for everything we paid for her to prove we provided more than half her support. It's definitely worth restructuring if you can make the numbers work!