My wife and I have done all the terms (short, mid, long term rentals) and have done some live in flips.

Thank you for a lively debate.

BTW, it is illegal for a seller to receive any proceeds from the short sale,  however,  they may be qualified for relocation $$$ or other reimbursable expenses.   

Just google the following: - special assessment - zombie condos - Florida condos (look for recent news)Since you are not living near the properties anyways, why not look in a landlord friendly state where the purchase prices are lower?

They are really changing the shape of the city and it may become incredibly expensive to buy out there soon due to lack of housing.

If that is the case, then you are good to go.Next thing will be to not rent anything until you get a real live lease and rental agreements.

Constructed in 1910, this property features a total of 2,793 square feet of living space.

We are currently living just south of Boston and are looking to purchase a 2-4 unit property in which we would live in one of the units.

Those can indicate poor management, deferred maintenance, difficult and expensive upkeep like ocean front which will bring up issues with rising oceans, insurance, and hurricanes. 

If the eviction goes to court, then there is a record of that eviction on their file and it will make it harder for them to find another place to live (assuming the landlord does a background check).Not renewing the lease happens when either party decides they simply don't want to renew the lease.