Newbie here and I'm sure I'm overthinking things but I want to set things up properly from the start. 

First, what does everyone use? Quickbooks? I do plan on using an accountant, so maybe I don't really need QBs?

I live in one state but am making my first investment property purchase in the state where all my family resides.

I will be getting rental income, so do I need to start an LLC in that state for tax purposes? For every state I plan on having property in?

Thanks for your input!

Quickbooks is best if you plan on scaling. I think it offers the best optionality. I also think Stessa is good from what I hear. As an accountant who prepares taxes, I don't really have a preference. The biggest thing is to be organized and have everything ready for your accountant. By doing this, it will also save on your tax bill. 

If it's a single member LLC, it's what called a disregarded entity and it just goes onto to Schedule E. If it's multi-member, you'd want to consider. If you did create an LLC as a single member, it'd be primarily for liability purposes.

Thank you for your insight, Aaron!