(elevating the properties, etc.)Ryan

The Elevation of the lowest floor house compared to the flood level has a big impact on rates. 

The rates are standardized and broke up by type of building (residential, commercial, condo), flood zone, elevation, and other factors. 

Also, when you tear off the brick to get to the drywall-like sheathing I would go back with lapped cement siding (if restrictions permit), much cheaperJust be sure you get a certificate passing mold visual inspections and air quality and that they also provide you with an 'Insurance Stamp' (what they called it anyway).I'm guessing the home's elevation versus the BFE checked out in that area? 

Think "elevator speech". 

I can't speak for the norm in Ocean City, but here you have two separate expenses: 1) Your HOA fee which covers utilities, building insurance, maintenance of the pools/elevators/etc; and 2) Your management fee. 

My builder (in Texas) applied german schmear on the front elevation (brick) of our new house under contract without our knowledge.

We're maybe a quarter of a mile from Clear Creek, but its about 30-40 feet below us in elevation.

I'll even throw in a brand new AC and water heater and you're still nowhere close to $30K.I think you can elevate the value, improve the cap rate and not risk $30K.

This article, "Fix your elevator speech"http://www.inc.com/marla-tabaka/fix-your-elevator-speech.html did makes some good points.