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.

I tried looking at their help articles but they're not very detailed about my specific situation with multiple 1099s. Did you have multiple income sources? Also, did you find their interface for business expenses intuitive?

I had three different 1099s last year from different clients. Their help articles on combining multiple 1099 forms on Schedule C were really helpful. You just need to enter each 1099 separately, and the software combines them correctly. For business expenses, I wouldn't call it super intuitive, but it's organized by categories that match the Schedule C form. The trick is to pre-categorize your expenses before you start (office supplies, software, equipment, etc.). Make a spreadsheet first with everything sorted, then the data entry goes much faster.

Do you pay the quarterly estimates online or mail in the vouchers? I've been confused about which is better.

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.

Are there any gotchas with these out-of-state trusts? Like do you need to visit that state regularly or have some connection to it? Just trying to understand if there are hidden downsides.

Yes, there are definitely some potential "gotchas" to be aware of. First, you'll need some legitimate connection to the state - typically this means having a trustee (individual or corporate) who resides in or has a significant presence in that state. Simply naming a friend who lives there isn't usually sufficient. The second big consideration is ongoing administration costs. Out-of-state trusts often require hiring a professional trustee or trust company in that state, which can cost anywhere from $2,500-$8,000 annually depending on the complexity and trust assets. For smaller trusts, these fees might outweigh the tax benefits.

I did some shopping around for a South Dakota trust last year. Initial setup with a decent trust attorney was about $5k, then annual trustee fees with a SD trust company were $3k. But I was putting significant assets in it ($3M+) so the math worked out in the long run. Probably not worth it for smaller estates.

Normally yes, 529 contributions are subject to gift tax limits (currently $17,000 per donor per recipient annually without filing a gift tax return). However, qualified rollovers from one education account to another are exempt from these limits. Since this was a rollover from a Coverdell ESA to a 529 for a qualifying family member, it doesn't count against the annual gift tax exclusion - it's treated as a transfer of an already-existing education benefit rather than a new gift. That's one of the many advantages of doing a proper rollover rather than taking a distribution and making a new contribution.