Plus, I won't yet have the cash to update the larger house so not sure how many vacationers want a dated place.

When research markets for things like demographics, wage growth population growth , and attracting the creative class; what websites or specific data do you pull where do you get your information and what numbers and specific trends do you look for most when choosing to invest buy and hold wether commercial or residential?

Irregardless of your answer to the above questions you will want to position the property for its highest and best use, which will in turn attract the largest tenant pool. 

Attractive past returns might not be reflective of future returns.

In florida, people spend time outdoors so this is attractive but likely not a deal breaker.

They could sell the first position note (which would be at an attractive rate) and hold the 2nd (which would be as close to negative as I can get it) but even then running 19 buildings for a few grand a month seems pointless when there's easier money here. 

However, the sell price is looking attractive.

Since supply is less than demand, homes will be higher priced and more attractive to the sellers in the market.

But all in all the quality of new housing developed during that period is subpar : cheaply built and poorly designed.On the other hand, the Altbau (pre 1953 construction) inventory in the East remain significantly more attractive.

The vacationer with a minimum of a 1-week stay?