The only maintenance that I can see it requiring is lawn care and pool maintenance.

Be careful.

I would be very careful and look at the condminium association itself to see how they are governing the complex.

I am looking at a 3/2 house that is well taken care of that I am looking to house hack, if the price is right.

The idea is to own enough rental property to support me when I need the extra help, fund my retirement, keep my parents healthy, and take care of my possible future family.

This is because it is largely tourist based and in recessionary times, one of the first things cut is discretionary travel.  

The tenants of that property didn't seem to take good care of the property, so that kind of questioned the type of tenants we would attract in the area. 

Derek, You need to hire a Property Manager as soon as possible, the ROI restrictions will hurt more by neglect and vacancy than by paying a PM to take care of these things for you.

Several major health care corporations have moved their headquarters to Nashville.

It has been very well taken care with the major nuts and bolts like the windows, roof etc being in good condition currently but it was basically treated as "if it's renting and not broke don't fix it".