I’m really early into the research phase but would be prepared to “pull the trigger” over the winter (eg purchasing a property to setup the tents) but ran into a bit of a “wall”.I’m pretty close to Blue Ridge and love the area so have considered a STR there for a while.  

I took down every interior wall and completely changed the Floorplan.

The garage probably doesn't have any plumbing, so this is from a roof leak.The wall probably has mold inside it.

I've met with my architect And she says  "Drawings will include beam schedules as required by The City (for opening up the walls).

Unless this is a wall oven, most ranges are a standard size.

I'd look for signs of arcing around those outlets.Other things I look for are how is the foundation, cracks in the walls (assuming lath and plaster), condition of the mechanicals, depending on what the house is built on, I may get a radon test done for the air and water (near me there is a lot of ledge, so radon is an issue in most homes). 

Quote from @Jaron Walling: We're still renting my first property from 2018, have cash-flowed every month, and "lost" every dime replacing the HVAC this year.

So I’ve since blocked off the third floor on one side and rented it as a 1 BR for now. but when the other side leaves eventually I’m starting to lean towards raising the ground grade 28” so that the total drop is less than 20’and then I’ll knock down some walls and make the whole 3rd floor attached only to that last unit so that the whole area can use the stairs and that window as second egress. 

Also, the city's building code could be different as far as the required fire rating for party/shared walls, etc, thus the construction costs could be higher.

I got future walls done with wood panels as well as paint and wallpaper put up.What was the outcome?