Seems like there would be more issues / risks to take into consideration and I wanted to get thoughts from those that have rented property with waterfront access.

I will state first see an attorney who is experienced in putting together entities.In the operating agreement is where you are going to want to put the accountablity issues front and center.

Looking at properties that are built in the late 1980's to help cut down on maintenance issues, I hope.

No issues, just the floor is pretty cold in winter.

The biggest issue you may run into would be if that the home he has already is an owner occupied home?

It is time to embrace the technology and work with it.

Lease Options can be tricky in some States (Texas for example), so make sure you're aware of any issue's before getting into the contractual stage.Whats your timeframe to put the deal together?

So basically the hurdle of "will I make enough the first year to pay the mortgage" won't even be an issue, the land is already owned free and clear and we can  "buy it slowly with profits". 

We issue Notices to Vacate on the 7th (first time offenders) or 2nd (repeat offenders).In our lease we are clear that payments from the tenant are applied to the oldest amounts owing first.  

Sounds like the agent did not do a background check or hid things about their background from you which is another issue, but nothing you can do about that now.