You do have time and motivation and muscle, but sometimes these turn into a lot more work than meets the eye. 

because bulldozers are popping up in the most unlikely places...I'll keep keeping my eye out.

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

The rest, is really just predator protection, how to not be a juicy rib-eye out wandering the savannah tempting a lion to pounce, and/or putting a moat around things so it's a whole lot harder to near impossible for them to do so.

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

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

Think about it now with the new brokerage laws where buyers are expected to pay brokers fee's if they are not paying thousands to mortgage brokers it leaves them more money to pay their Agent who actually finds the house for them helps them with insprections etc etc.. buying that home in British Columbia really opened my eyes to how goofed up our owner occ lending process is .. and costly.

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 ?

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!