Quote from @Blaise Peterson: Daughter: 26yo and earns >100k/yr and, historically, has rolled her eyes when I mention the phrase "real estate".

But you're living in a market people are keeping an eye on from all over the east coast! 

I do like real estate, I have a great eye for design, but would hate to have to evict someone—that would be my worst nightmare, so I’m not sure I’m cut out for being a landlord (although I would fully anticipate having a property manager)Is option #3 a far inferior option compared to keeping our expensive house in expensive city as a rental and only having to deal with one property that gives us great appreciation in 10 years ?

Its certainly a very precarious situation for these companies managing there reputations..Which in todays world of SM can be wiped out in a blink of the eye or a stroke of the keyboard..

4) Would It be easier to borrow that money knowing that I am trying to provide affordable housing in the governments eyes?

Keep an eye on local developments that could boost property values.4.

@Garrett Brown glad to know we see eye to eye on valuable STR content and proper spelling! 

Second, be sure to keep an eye out for owners with multiple homes in an area.

I’ll still keep my eye on it.  

By the time we came back security had pepper sprayed the gang leader and he ran into one of the rooms after breaking the glass and rinsed his eyes out and ran away.