Thanks, this is really interesting! I hadn't heard of the Series LLC before. Is this available in most states? And would each owner still get a K-1 showing their specific income after their individual expenses?

Series LLCs are currently available in about 20 states including Delaware, Texas, Illinois, and Nevada (among others), but the laws vary significantly by state. Even if your state doesn't allow them, you can form one in a state like Delaware and register it as a foreign entity in your home state, though this adds some complexity. Each owner would still receive a K-1 reflecting their share of income based on the operating agreement terms. The operating agreement would specify how individual expenses are accounted for before calculating each person's distributive share. This approach gives you the liability benefits of separate entities with the administrative simplicity of a single filing.

I wouldn't recommend a general partnership for this scenario. Without the LLC structure, all partners have unlimited personal liability for business debts and legal issues. That's a huge risk with 10 different people involved who all have separate business activities! An LLC provides crucial liability protection that a plain partnership doesn't.

If I file now but can only pay like $500 upfront, will the IRS automatically put me on a payment plan or do I have to apply for that separately? I'm in a similar situation with 2022 taxes.

You need to specifically request a payment plan - it's not automatic. You can do this when you file by submitting Form 9465 (Installment Agreement Request) with your tax return. Alternatively, you can file first and then apply online for a payment plan through the IRS website if you owe less than $50,000. For amounts under $50,000, the online application is pretty straightforward and you can choose your monthly payment amount (as long as it would pay off the balance within 72 months). There's a setup fee that varies based on how you apply and pay - it's cheapest if you apply online and set up direct debit ($31 setup fee vs. $149 for applying by mail/phone with other payment methods).

How much did u end up owing if u don't mind me asking? And did u get any penalties reduced?

Thanks for bringing this up! My parents and I already discussed this - they aren't claiming me as a dependent this year since I provided more than half of my own support. I've been working almost full-time hours at the restaurant plus some gig work on weekends. So I should be able to claim my own education credits, right? Is there anything specific I need to document to prove I supported myself in case of an audit?

Yes, if you provided more than half of your own support and your parents aren't claiming you, then you're absolutely right to claim your own education credits on your return. This is actually the ideal situation for maximizing your benefits! For documentation, keep records of your income (pay stubs, bank statements showing deposits), housing payments (rent receipts), and major expenses throughout the year. Also track any financial aid, scholarships, or loans in your name. You don't need to submit these with your taxes, but having this documentation is important if you're ever questioned about your independent status. A simple spreadsheet showing your total income versus your total expenses for the year can be really helpful to demonstrate you provided over 50% of your own support.

I had the same issue last year! Turned out the Premier version was correctly applying some course material expenses that the Deluxe version missed. Worth double-checking all the education expense sections regardless of which version you use.

That's a great point I hadn't considered. I acquired the shares in three different grants over about 2 years, with different purchase prices. Would I need to specifically tell my broker which lots to sell, or is that something I can handle when I file my taxes?

You need to specify which lots you want to sell at the time of the sale - you can't decide later when filing taxes. Most online brokerages have this option during the trade execution process, usually called "tax lot selection" or something similar. If your broker's online platform doesn't make this obvious, call their customer service before placing the trade. Once the trade settles, you typically can't change which lots were sold, so it's important to get this right the first time. This kind of specific lot identification can make a substantial difference in your tax situation.

This is good advice. You can offset up to $3k of ordinary income per year with capital losses beyond what you use to offset gains. So if OP doesn't need to offset all $87k in gains this year, they could realize some losses now and carry the rest forward.

Does this apply to FreeTaxUSA too? I switched from TurboTax this year to save money, but I'm worried the cheaper software might not handle these details correctly.

Yes, FreeTaxUSA handles Schedule B the same way. I actually switched to FreeTaxUSA two years ago after using TurboTax for over a decade. Their interface for entering 1099-DIV information is straightforward - you just enter "Vanguard Brokerage Account" as the payer name and the total amount from Box 1a. The software will automatically generate Schedule B if you're over the $1,500 threshold. FreeTaxUSA is actually quite robust for most tax situations, especially for investments. The only real difference I've noticed is that the interface is a bit more streamlined, but all the functionality is there.

That makes sense! My sister has about 8 different funds, so I can see how that would get unwieldy. Sounds like this is standard practice and not something unique to Vanguard. Appreciate everyone's helpful responses - this has been really educational for both of us!

Exactly! And if your sister has multiple brokerage accounts, she would list each brokerage separately on Schedule B. For example, if she has Vanguard and Fidelity, she would have two entries - one for each brokerage with their respective totals from Box 1a of each 1099-DIV. The IRS matches these totals with what each institution reports, not the individual holdings within each account.