Thanks for this insight! My syllabi do list specific shows/performances we need to watch for class discussion, but they're across different platforms. Would it help if I got a letter from my department stating these are required materials for my degree program?

Yes, documentation from your department would definitely strengthen your case if you're ever questioned about these expenses. Ask your department to provide a letter stating that access to these specific streaming platforms is necessary to complete required coursework for your degree. Keep in mind that the IRS might still only consider the portion directly tied to specific required viewings as qualified expenses, not the entire subscription. So detailed records of what you watched for class requirements versus personal viewing would be important.

Do textbooks and software count toward those credits too? My tax software never asks about anything except tuition payments.

Yes! Textbooks, supplies, equipment, and software that are required for enrollment in your courses absolutely count toward these education credits. Many tax software programs don't prompt specifically for these, which is why so many students miss out. Just make sure you have documentation showing they're required for your courses (like a syllabus or course materials list). Keep all receipts and documentation for at least 3 years after filing in case of an audit.

I didn't see any supplemental info but I'll double check! I was just looking at the downloaded PDF without really checking if there were additional pages. That's a really good point. I did notice there's a tiny footnote at the bottom of one page that mentions something about basis reporting, so maybe that's related to what used to be on line 12? I'll look more carefully through all the documents they provided.

Definitely check for those extra pages! They're easy to miss, especially if you downloaded the forms. Sometimes they're separate files or included at the end of the PDF. The footnote you mentioned sounds promising - those often contain important details about how the brokerage reports certain information. Also, most brokerages have a "tax help" section on their website that explains how to read their specific versions of tax forms. That might give you the exact mapping from their form to what your tax software is asking for.

Yes! The IRS redesigned several tax forms for this filing season. I think they're trying to make them clearer but it just causes confusion when you're used to the old format. My accountant said it happens every few years.

If they file an extension, do they miss out on getting their refund until October? I'm confused about how that works with the payment vs. filing distinction.

If you're expecting a refund, you won't get it until after you file your complete tax return. So yes, filing an extension would delay your refund until whenever you actually submit your completed return (which could be anytime between now and October 15th). The distinction is important for people who owe taxes. The extension gives you more time to complete the paperwork, but you still need to pay what you estimate you owe by the original deadline to avoid penalties and interest. But since you mentioned having a new child and home purchase, there's a good chance you qualify for additional credits and deductions that might result in a refund.

I used FreeTaxUSA last year when we bought our house! It was actually pretty good for the price. The interface isn't as slick as TurboTax, but it walks you through everything step by step. The only thing is you have to know what forms you need - it doesn't really give advice about your specific situation like a human preparer would. But for $7 it was totally worth it.

Do they have good support if you need help? I always worry about getting stuck on something technical with the investment reporting.

TaxHawk and FreeTaxUSA are actually the same company, just different branding! Both handle investments for free federal filing. I switched from TurboTax to TaxHawk two years ago and saved around $75.

Wouldn't I still be personally liable as a sole proprietor though? That's my biggest worry - if someone gets hurt at one of our events or something else goes wrong, I don't want to risk my personal assets.

Yes, you would be personally liable as a sole proprietor - that's the main drawback. If liability protection is your primary concern, then an LLC does make sense. In that case, I'd still recommend keeping it as simple as possible with a single-member LLC unless your friends are insisting on being official partners. Make sure you get proper event insurance regardless of your business structure. Even with an LLC, if something goes wrong at an event, having good insurance is often more practically important than your business structure, especially for small businesses where people sometimes accidentally "pierce the corporate veil" by mixing personal and business finances.

S-Corps are so overrated for small businesses. The accounting and payroll costs eat up any tax savings unless you're clearing like $75k+ in profit. Plus you have to run actual payroll every month which is a pain.