You are a beginner in REI – so get started first, accumulate some equity, get some serious cashflow going, get some experience with managing real estate, figure out you want to do this long term…and then worry about how to layer an LLC cake.

I've done it, and so I believe I can say something useful about it.You mention in your profile that you have 20 years of experience as a contractor.

Also since you have ZERO experience, I strongly suggest a big NO.

Does anyone have any experience there?  

Does anyone have any experience with raising private money for STRs?  

Particulars:1) 1st SFH rental property cash flows $400 and we have a 2 year lease agreement that ends in 2025. 2) 2nd SFH I currently live in, I would rent out and probably experience a negative cash flow of --$100 cash flow for first year, break even 2nd year, and build little cash flow moving forward.

Agree with others, if you take the plunge and self manage for a year or two, it’s a great learning experience, then just outsource to PM when you start scaling.

In my experience overall- costs are going to be higher.

If a cash out refinance, many lenders will allow the cash out to satisfy the reserves requirement.DSCR lenders generally let you vest either individually or as an LLC.

Have you considered renting out individual rooms in your current home instead of renting out the entire property?