But aren't there still some above-the-line deductions that you can take even if you don't itemize? I thought stuff like HSA contributions and student loan interest didn't require itemizing?

You're absolutely right about above-the-line deductions! Those don't require itemizing and can be claimed in addition to the standard deduction. Common above-the-line deductions include HSA contributions, student loan interest (up to $2,500), certain IRA contributions, and self-employment tax. These appear on Schedule 1 of Form 1040 and reduce your adjusted gross income directly.

The IRS recommends keeping records that support income, deductions, or credits for 3 years from when you filed the return. But if you underreport income by more than 25%, keep records for 6 years. For property records (like your home), keep them until you sell the property plus 3 more years.

8 Does that work with W-2s too? My HR department acts like they're guarding state secrets whenever I ask for anything.

11 It's less consistent with W-2s because larger companies often use third-party payroll processors that release all forms at once. But smaller companies that handle payroll in-house might be able to generate yours early if you explain why you need it. With financial institutions like banks and investment companies, they're usually more flexible because they generate these forms on an ongoing basis. Your HR department probably has stricter policies because they're dealing with everyone's payroll data at once.

18 Some employers don't participate though. Mine shows up as "not available" every year and I have to wait for the paper copy like it's 1995 or something.

Is that really true about the training? I always assumed those places had actual accountants or something. How do they get away with charging so much if the people aren't even experts?

Yep, 100% true. The training at the place I worked was just a few weeks long. Some locations might have a manager with accounting experience, but many of the seasonal preparers are just people who completed the company's basic training program. They're trained to use the company's software, which asks the same questions online software asks you. They charge so much because of overhead (physical locations, staff, etc.) and because many people don't realize they're mostly paying for data entry rather than specialized expertise. The companies market themselves as "tax experts" which gives a false impression. For complex returns, you're better off with an actual CPA - and for simple returns, online filing is usually just as accurate but much cheaper.

Yes! I used Free File last year through TaxSlayer since my AGI was under the limit (around $73k). The interface was exactly the same as their paid version, just free. It handles W-2s, simple self-employment, and basic deductions fine. The only annoyance was having to go through the IRS website first to access it - you can't just go directly to the company site or they'll try to upsell you.

Thank you so much for this breakdown! Would a letter from the bank managing the UTMA count as documentation that it's restricted? And do we need to report the balance of the account or just that it exists?

A letter from the bank would definitely help! Ask specifically for documentation stating it's a custodial account with withdrawal restrictions until you reach the age of majority (18 or 21 depending on your state). You generally need to report both the existence of the account and its current balance. However, the good news is that even though you're reporting the balance, the agency will likely classify it as an "excluded asset" based on the restrictions. Make sure to keep records of everything you submit, and if possible, get written confirmation from your benefits caseworker about how they're classifying the account. This documentation will help if there are ever questions in the future.

Did your grandma have to file any gift tax returns when she put money in your UTMA? My parents are worried about that part.

That's a great idea about checking bank statements! I just looked and the deposits do show a slightly different name than what I was using. I'll try searching for that. And thanks for the reminder about expenses. I've been tracking most things but I'm not sure about home office deductions. Does anyone know if it's worth claiming a home office if I use my dining room table for most of my freelance work? I don't have a dedicated room.

For home office deductions, the IRS requires that the space be used "regularly and exclusively" for business. Unfortunately, a dining room table that's also used for family meals wouldn't qualify under the strict definition. However, if you have a specific corner or section of a room that's used exclusively for your business (like a desk in the corner of your living room that's only for work), you might be able to deduct that portion. Just be careful with home office deductions as they can increase audit risk. If you're using a simplified method, you can deduct $5 per square foot up to 300 square feet without having to document actual expenses, which might be easier if you do have a dedicated space.

In my experience working as an admin for a small business, sometimes the EIN is hidden because they messed up and sent you the copy that was supposed to go to the IRS (Copy A is typically red and has the TIN partially masked). If that's the case, they should have another copy to send you.

I didn't think about checking the envelope - unfortunately I already tossed it. This is my first time doing work for them so I don't have previous forms. I checked their website but didn't see any EIN listed. You might be right about them sending the wrong copy! The form does have a reddish tint to it, which seems unusual. I'll mention this specifically when I follow up with them again. Thank you both for the suggestions!