Winning requires dedication and immersion within the program, the culture and also networking within your local and virtual communities to create as well as receive value.  

It also depends on the commuting culture of that city, in the Bay Area people will pay HUGE amounts to live close to the tech jobs.

(A lot of people, young, vibrant)Austin/Portland (I like their eccentric culture, but don't love them because I'm more into diversity at this stage)However, I've found it hard to find a place that matches the critieria: Under 400kMulti-UnitUrban and YoungGood rental or Airbnb marketGood investment and growth to followThe best contender so far would be Chicago where some duplexes surrounding Hyde Park (mainly South of it) near University of Chicago seem to have some affordable multi units.

In my humble opinion... after living in Puerto Rico 20+ years and becoming very familiar with the political, economic and cultural situation of the island (after all I AM puertorican), I strongly believe that what the future holds for Puerto Rico is very similar to that of the Dominican Republic.

There is also a style of home called contemporary that uses cedar siding.What your are asking for 4 and 5 is very subjective and localized.

@Gene Livingston, @Hattie Dizmond I understand a lot of people use leverage (debt) whatever your choice word is, and it's become the culture.

They are two magical islands where the cultures have been pressure cooked.

As s for overkill on the subject, It seems NYS is a very litigious culture and I lean toward the advice from @Calvin T.  

The drain line is leaking underneath the sink where the rubber gasket gets screwed into the underside of the cultured marble sink/counter.

I expect the nearest similar case is Rome; similar debasement of currency, similar taxation, similar foriegn entanglements, similar culture.