Do the free fillable forms on the IRS website count as e-filing? That seems like a good middle ground where I could still fill everything out myself but submit electronically.

Yes, the free fillable forms definitely count as e-filing! That's exactly the perfect middle ground. You'll still need to understand each form and calculation yourself (unlike with TurboTax which handles that for you), but you get the benefit of electronic submission. This way you still get the educational experience of working through the forms manually, but avoid the massive delays of paper processing. Plus, the fillable forms will catch basic math errors, which is helpful when you're learning.

I've heard about that program before! Do you need any special qualifications to volunteer, or can anyone sign up for the training?

This is super helpful! I hadn't even thought about the dependent thing. I am still living with my parents and they pay for most of my stuff, so I'll definitely check with them about this. Is there an easy way to calculate how much I should be setting aside each time I get paid? I'm making anywhere from $150-400 a week depending on how many gigs I pick up.

A simple rule of thumb is to set aside 30% of everything you earn. That should cover both your self-employment tax (which is about 15.3%) and your federal income tax. If your state has income tax too, you might want to bump that up to 35%. The easiest way to manage this is to open a separate savings account just for taxes. Every time you get paid, immediately transfer 30% to that account and don't touch it. At tax time, you'll have the money ready to pay what you owe. Plus, if you end up owing less than you saved, you'll have a nice little bonus!

This is so important! I got slapped with a $420 penalty my first year freelancing because nobody told me about quarterly payments. The IRS doesn't play around with this stuff.

I didn't know about checking that box! Will that really help? And I don't have kids, so I'm not sure about the tax credits. I'm filing as single.

Yes, checking box 2(c) on the W-4 helps when you have similar-paying jobs. It basically tells your employer to withhold at a higher rate to account for your total income being higher. Even without kids, you might still qualify for EITC depending on your exact income. With your combined jobs totaling around $52,000, you might be just over the limit for a single filer, but it's worth checking. There are also education credits if you're taking any classes, or the Saver's Credit if you've contributed to a retirement account.

This is what I've been doing for years with multiple jobs. I have them take an extra $100 per paycheck from my main job. I'd rather get a refund than scramble to pay a bill in April!

Thanks for the specific guidance on Taxport Convey! I found the "Review Exceptions" option and it shows all 42 errors in one place. If I implement the 90-day grace period approach, will I need to go back and amend these later if we don't receive the TINs within 90 days?

Yes, if you don't receive the TINs within the 90-day period and you've applied treaty rates, you would technically need to file amended returns using the higher withholding rate (typically 30% for Chapter 3). However, there's an exception for certain passive income, including some types of dividends, where you may be able to continue applying treaty rates if you have other sufficient documentation. I would recommend documenting all your follow-up attempts to obtain the TINs. If you can show reasonable efforts to obtain the information, it can help if there's ever an IRS review of your filings.

Publication 515 was super helpful when I was learning, but it's like 100+ pages. Any tips on finding the relevant sections quickly?

Have you used it for reporting inherited stocks? That's the part that's tripping me up with my grandma's investments. Need to make sure I get the cost basis right.

Yes, I've used it for inherited stocks. It handles the stepped-up basis correctly - there's a specific section where you can indicate the shares were inherited and enter the fair market value on the date of death as your basis. It also has a surprisingly helpful help section that explains the inheritance rules clearly. Way better than some of the more expensive options I tried previously that made this unnecessarily complicated.

TaxHawk and FreeTaxUSA are actually run by the same company! So if FreeTaxUSA doesn't support certain forms you need, TaxHawk probably won't either. They have identical limitations on which tax situations they support.