These caused damage that couldn't be seen in my inspection of the MH.  

It might sound unreasonable but if you stepped on the agent's sensitive toe, then containing the damage is important.

Please note that windows damage is usually tenants responsibility unless otherwise is written in the contract.

The damage is $500 for a 3 mth listings.  

In addition, there are separate legal requirements for handling a security deposit, the failure to satisfy any one of which subjects the landlord to TRIPLE damages if it is raised in court.I just did a quick check for NY, and it appears there is no statute in regard to prepaid rent:NY Rental LawsBUT, when it comes to landlord-tenant law, it pays not to assume anything, so I'd strongly recommend contacting an attorney for a definitive answer.

If bank is claiming 80% and no tenant seasoning on a bunch of new tenants to increase occupancy then you need to assume they will default and damage will happen to the units.

However when it comes to condos HOA takes care of these things:maintain all structures, such as patching damaged roofs and siding, for example.

I will definitely stay on the look out for damage.

You are right considering that a tenant could severely damage your house.

I wouldn't take 2 rentals and a primary home into a closely held corporate structure unless there was a good business or estate planning reason to do so, you probably don't need the additional brain damage.