Live in one unit , rent out other unit and accessory unit, mortgage on the property would be about $6800, rental income would be : $3000 from additional unit , and $1500 from accessory unit and I would be occupying one unit , leaving me at negative $2300 per month .

Anything structural (adding/taking away walls or square footage)6.

Unfortunately, this isn't always an easy relationship.What if you, as a buyer, like a home but despise its wood-paneled walls, shag carpet and lurid orange kitchen?

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).

You won't know until you open up walls.

I’m thinking of Getting financing to build accessory dwelling units with new adu laws starting Jan 1 2020.  

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).