The selfish part of me just also wants a single family that needs some cosmetics  for me and the dog to have some privacy, then move out and rent it.

Not to mention that holding properties overseas can have tax and privacy advantages.

They want a comfortable desk and office chair and, ideally, they want it in a room they can close off from the rest of the house for quiet and privacy while in meetings.

Dorm rates are high, with no privacy...so I had an idea.

Hi all - what do others do when assessing a smaller property (< 0.5 acre) that has multiple standalone structures that could be rented separately but they do not have great separation for privacy?

When they ask you to replace the chain link fence with a 6-ft cedar privacy fence, it will be hard to say no.3.

Other things to consider are Personal Injury coverage (Libel, Slander, Wrongful Eviction, Invasion of privacy).  

And specifically, am I better off getting a full-time renter, or doing a short term rental (which I think I would prefer so I can have privacy when I wanted)?

There are some additional benefits outside the reduced liability component, particularly for holders - like owner privacy/reputational risk and tax efficiency using the strategy that Joshuam alluded to.

You would pay transfer taxes three times and perhaps mess up the privacy and entity you hoped to build.