My hangup is that even though the HOA is not allocating $85k for the reserved this year, they will have over $200k in reserves (over 20% of the $850k budget) Everything else has been cleared by the underwriter (insurance policy, occupancy rate, ect..) but I am concerned this deal will fall through because of this issue. 

I'm looking for a good insurance agent for landlord insurance policy!

You need a short term rental policy.

We took this disaster personally as we love Asheville and have visited many times.When there's an official presidential disaster declaration (there was), flood insurance policy holders should apply for FEMA assistance in addition to their flood insurance claim.

Or, is it worth just getting an umbrella policy to cover all properties?   

Any ideas on which policy might be the best fit?

For example, if a state enacts a law that prohibits individuals from having boats on their property, the state would then enforce that restriction.If the restrictive covenant governs an entire condominium building or a subdivision, they are enforceable by one or all of the property owners in that community.

However, I like the idea of the guaranteed rental income from the government.

I contacted the government (province as they are in charge of this) to ask and was told that I didn't need to pay for the modifications. 

I know for certain there are professional PM's that stopped listing on VRBO a few years back when they changed their policies, but I don't know those PM's well enough to get the relevant data.My first inclination was "I need 5% or more increase in occupancy to make it worthwhile".