Hoping to get into a small multifamily property (duplex, triplex, or fourplex) that may require some work but not too extensive.

Lots of great answers on here - especially going to DSCR - one thing I wanted to add is as part of your hard money loan, see if they have option for 3 or 6 month extension.

There is a contract signed by the previous owner for 5 years with 10 automatic extensions, so the contract expires in 2024. 

Let her know you'll send her to collections if she refuses. 

To avoid opening a bank account and following all the rules that come with collecting and holding a security deposit I figured id just treat last months rent as security deposit.

What’s the legal way to collect payments from roommates that live with me in the same house? 

The LLC collects rent, pays expenses, and distributes funds to the owners based on your partnership agreement.

It's completely legal that's what I do I pay the bills to the utility company and send a copy to the tenants and collect the 60/40 split from them each month

They now collect that informaton at the birthing hospital. 

I'd also suspect that as an owner-occupant, one might be able to skirt strict STR laws, and rent out a primary in an extremely in-demand market, especially in the near-term (think collecting huge fees seasonally around CU football games the next few years).