2) Did you intend to operate it as a short term rental, but then plans changed once you learned the CCRs only allow terms of 6 mos or more? 

However, you saved $24,000 by paying a lower premium for the last five years so you actually have $34,000 towards the roof replacement. 

How is short term rental business out there?  

We want to go for another real-estate investment (we are doing buy and hold..buy low, renovate and make them short term rentals on airbnb in Ocean City, Maryland).

I like the idea of short-term rentals, and I am wondering if I would be better off buying several smaller, less expensive units, or one larger, nicer unit.Those of you with experience in the Airbnb Marketplace, what are your thoughts?

You are not too familiar with the area, so if your short-term stay is near an airport you have less travel time and can spend less on taxis.

The only thing I'll note, because I work in the insurance industry, is some companies give a discount if you pay the premium in full (which the escrow does). 

Any tips or ideas regarding forms or documents I should give them shortly after close?

I saw that you said the property manager has a lot of experience with turning units to get them reno’d so maybe the additional 6 months to a year of rental premiums could be your hedge on that $50k in repairs that needs to be completed, as long as it makes sense for you guys.

My family member is about to lose her house to a short sale.