Have ALL of your ors in the water, do/setup marketing in many channels (SMS, post card, PPC), learn how to carve out lists that target motivation that you want. 

Are there some strategies here that I am missing in filtering through potential properties? 

Saving for DP and repairs, maintenance, vacancy, water, taxes, insurance etc.

We have 45+ pads which are Water, sewer, electric connect ready.

The property has been rented for nearly this entire time.The house has a good amount of deferred maintenance, is not updated, and has some water damage which we only recently (two weeks ago) became aware of.

For Fire damage, smoke damage, black water, broken pipes and other disaster clean ups we recommend Jim Seubert @ Pride Cleaning and Restoration 618-792-0465.

How should I tell him to terminate his electric, water, and garbage bill? 

Eligible property includes 1) Computer software that is depreciable 2) Qualified leasehold improvements property 3) Water utility property and 4) MACRs property that depreciates over 20 years or less.

Kitchens need remodeled every 10-15 years to maintain high rents, roofs go bad, HVAC, water heaters, etc.  5% will likely not be enough to cover these items when they come up.  

It's not on the water, but walkable to  a beach and part of a HOA with marina (no deeded slip but access to boat ramp).