@Richard Davis Emailing an offer is not accepted to most sellers and will not be enforceable.

Seemingly minor procedural mistakes get the case thrown out and you have to begin again.In the short term, send him a letter and let him know there is a "new sheriff in town" and you will be enforcing the lease that is in place - including late fees, etc. - without exception. 

I think you’ve learned that oral contacts are hardly enforceable. 

You should also check with Code Enforcment as well to make sure there are any infractions against the property. 

HOAs typically can only enforce common area things and if decks are considered common area I would throw a weekly BBQ on the deck of the HOA president (no permission needed).

(I always thought a child could drown in a lot less.)Code enforcement finally had it removed after they attempted to use a 'snow fence' to meet the fencing code.Our Ins cancels/boosts premiums for pools & if we buy a property with an above ground we tear it down a.s.a.p.As far as tenant ins we often add their policy to the cost of our own, but in their name.

Take a look at local code enforcement as well, see what info they may have on abandoned properties they're tracking. 

We are zoned for the Town of James Island, so while STRs aren't "legal", they only enforce the ordinance if a neighbor complains.

Since I'm running several different real estate disciplines my days remind me a little of my old days in law enforcement when I'd run from call to call, wherever the emergency was.  

My wife is very easy going with the tenants whereas I try to enforce the lease (violations, late fees etc) and I try to make decisions from a professional point of view, not personal.