This definitely has revenue potential.The property also has other structures of value and amenities but these would not be part of the business described below.We will be able to add additional guest cabins and possibly our (retirement) home in the future.This is a rural area and about half of the property is AG-Exempt.

Even though you may have a close relationship with this individual, everything you've just described sounds like a perfect opportunity to be taken advantage of.

I had planned to amortize the points in the way you describe.

everyone wants what you're describing - an easy cosmetic flip that generates cash for other purposes!  

From what you describe, tenants skipped town, I suspect they don't care about their credit either so you will have to file in court.

Any competent plaintiffs attorney will bring in all entites  Glenn described and argue an alter ego exists to latch onto whichever entity has the insurance or assets that are easiest to collect upon.

You did not fully describe your situation and what you did.

Most will not under the scenario you described most of us that do this infill need to pay cash before the bank will give us vertical they want the land brought in as equity ..

I realize I am not rich by any means but I want to describe my situation so an experienced REI can give me advice suited to my specific situation.

The way Avery Carl (the author) and the podcast guests describe it, managing an STR seems quite straightforward, though I'm aware it requires significant effort to be successful.My plan is to purchase a property for under $400k, make a 10% down payment, and self-manage it as an STR.Living in San Diego, and given the real estate prices in Southern California, finding a profitable STR locally seems challenging.