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.  

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).

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.

We replaced a lower roof and checked potential plumbing issues.

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

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

Everything from the window choice and wrapping to the flooring decision to the layouts and general roof pitch.

Roof, A/C, kitchen, bath, windows are all updated as of 1 year.

Then charge her pet fees, pet rent, additional deposit and additional rent for the extra people and demand a 2 year or longer lease.Then you can get them a second room and find a place that allows dogs.Red roof Inn is cheap.Maybe just do a couple nights while the bathroom is being redone and have contractor work around them for the other stuff Tell the contractor you'll give him a bonus if he can work longer days and finish sooner.