You're not going to cashflow on a water front property and you may have issues with seasonality and/or demand in a very tourist-driven area.If you have an idea of where you'd like to invest and what the numbers might look like, a good way to test the waters is to put an ad on craigslist showing a potential property with the rent you'd expect to get and see what kind of interest it gets.For my rentals in Louisville, over the past 6 years I've had anywhere from 2-3 emails a week to 30+ emails per day depending on the location, rental rate and time of year.

I really depends on how your are structuring the investment.  

I'm in Clearwater and can help you out depending on what contractors you need 

If you can have an addendum of removing the clause and seller is ok with it then you should be good.There will be local REI in NJ depending on your location where you can meet these guys.

So it really depends on what you can find.

Depending on your state law, you may have not allowed to accept it.

Just depends how passively you want to invest. 

Anyone have any contacts with dependable contractors in the Baltimore, Baltimore County area?

If it's a quite steep slope, you should budget $400-500/sqft, depending on finishes. 

Depends on what you want to do.