Different asset classes, different key metrics.

Cash flow upon closing is key.      5.

The key here though is if I had 50K to there is no way I would buy a house that breaks even. 

Other areas to look at would be near Siesta Key, Long Boat Key, etc... they are nice areas with frequent vacationers

That roof will be expensive, assuming there are gaps between the roof boards under the shakes, you will also have to sheet the roof, I would guess you are looking at $10-15K to do that roof

Economy finishes are available too (like those lovely 4x8 sheets of wall board with hundreds of trim strips).   

I think mace or bear spray on your key ring in your hand would be more effective.. 

Dan going forward I will not work with Touchpoint Property Management especially since they find it inconvenient to follow the rules and regulations that have been in place since 1984 and insist on insulating the Board and its members including me.

He has become a board member of the HOA to help control how the HOA money is spent.

@Mike Dorneman, I have done tons of similar projects. double-boarded homes are tough to work with.