I'm based in San Diego otherwise I'd offer to work with you but that would be a bit of a commute for you. 

I am open to both local and long distance as well.

No just trying to figure out if I could target hospital staff being within walking distance to the clinic.

We may use a property a couple weeks per year, so we're looking relatively close to home (within driving distance).

At least on the west coast if your within 30 to 45 minutes drive ( commutable) to the major job markets. your lot prices are going to be a minimum of 150k to 250k and up. 

i'm also a house-hacker; big fan. and i invest long distance in illinois, too!

When I told this "friend" what they did, he quickly backpeddled and distanced himself from him.

Also in Cali, I plan to do the long distance thing.

I would only buy a personal vacation/STR property if it was within driving distance such that you could use it for the weekend many times a year. if it involved flying, I would simply buy an STR for investment purposes and then vacation wherever we wanted.

Prices are high vis-a-vis incomes unless you're a Bay Area commuter.