What type of questions should I be asking and what questions are too intrusive to the sellers privacy?

I used @John Barrett: That was my best case scenario but finding a property with separate entrance for paying guest (I like my privacy) is almost impossible with my budget (700k)

In the back yard, I'm a HUGE fan of 6ft privacy fences, especially in rough areas!   

Granted, I'd say about 8% of the neighborhood doors had some sort of "Do Not Solicit" sign posted, so I respected their desire for privacy.

"I DEFINITELY do not want to spend years and years as a real estate agent"Bah it's a couple weekends of clicking next on a computer while you sip on drinks containing Rum in the privacy of your own home :)Not like getting a degree and darn sure without that cost!

This nets out much cheaper than buying a similarly sized 3/2 Single Family home and offers nice flexibility with the extra 1/1 unit for an additional renter, STR, or more privacy when family is visiting! 

I'd bet a lot of money the stack in the main bathroom is situated either in the middle or at the end of that privacy wall.With those problems in mind, the rest of it is going to be trying to put lipstick on a pig.

Hi, I was thinking buy repos, paint, repair or what ever needs to be done and place on a nice 1 acre lot I don't want it to look too much like a cramped park you know like I want people to have some privacy.

Utility companies may be less forthcoming nowadays maybe for privacy reasons. 

If he fails, that would be an issue.PS, make sure you don’t share anything you find in your screening process with your current tenant as that would violate expectations of privacy and could be a lawsuit.