For example there are 3 or 4 major utility companies just inside of Fayetteville and it seems like each property has a different structure/utility company.Other expenses = major capex (roofs, plumbing, flooring etc go bad eventually so I would save a monthly amount in a separate account for when these happen). 

The home will already have a view of the water from the front of home and would be a superior view to the roof deck since it is on the rear of the home.  

Insurance is going to get more expensive, the government wants to keep people in homes, home equity financing is only growing in popularity, multiple generations are living under the same roof more, and all of those trends are going to lead to changes in how tax law is used and possibly the law itself.

I’m currently trying to decide between two 3 bedroom units (one is roof top with gulf views and boat slip, other is ground floor with direct access to pool and big patio) , or a one bedroom in the same building that’s also roof top with gulf views (I believe sandpiper).

HVAC, roofing, foundation, plumbing, electrical are all mechanical items which would sway a deal. 

I recently have a water leak in a house.

But let me tell you about the roof leaks we have been having too. 

what kind of shape are the big and medium-ticket items in - roof, mechanicals, appliances? 

If there is a roof leak, you are likely to just repair it yourself rather than get insurance involved. 

They had no clue why and found out through their neighbor that the utility water meter was leaking.