This may have made me miss out on what would otherwise have been good financial investments, but it has also never failed me in having properties that attract decent tenants.

Do not fall for the attractive looking term sheet. 

It's becoming increasingly tough to justify these costs, especially when we see other listings in the area also struggling to attract tenants.

In today's market, many office landlords would much rather walk away from their properties and take a loss than fight to attract tenants and avoid foreclosure.

Will they still perform under terms that may attract a typical investor?

These updates included modernizing the interior, enhancing curb appeal, and addressing key areas to make the home more attractive to buyers.

Key West and the other keys does pretty well year round, relatively speaking; there's a lot of fishing attraction along the Keys even in the summer. 

Hoping for good neighborhood, good schools to attract low-maintenance family tenants. 

(on things like flooring, cabinets, remodels, siding etc) I want to hear thoughts on going as cheap as possible, making the house look "high end" (possibly attracting higher end renters and charging more) or somewhere in the middle?

Our 2/1.5s seem to go to traveling professionals (medical or otherwise), but our larger units attract the insurance company's attention.