There’s a lot of necessary back story): The small parking lot is ground level with asphalt, but it also acts as a ceiling to my building’s boiler room.

Do you know what they actually cost and how those systems need to be maintained and if they're legal in your area?  

I have a full month's security deposit, and they maintain the house well, so we're not talking about a crazy turnover. 

I would also recommend a local property management who is familiar with marketing and booking so that they can ensure your property is rented and maintained as much as possible. 

I would definitely raise the rent.The concerns I would have are: people that go to Hotels dont clean up after themselves so who would maintain the property?

It just shows an utter disdain for you and your business, and frankly a lack of appreciation for the effort you made to provide a well-maintained home at a reasonable price for he and his family.If he had responded more diplomatically, explaining he did not cause the damage and if he generally took care of the unit and was not a problem tenant, I might have been more inclined to work something out.  

We will need to fix the water heaters, replace the heating with heat pump AC/Furnace HVAC systems, replace the roof, redo the back stairs, install cameras, redo the landscaping, redo the asphalt, and install security doors.

My cuzzo drives dump trucks and he said maybe with a couple loads of asphalt and his skid steer we can fix. and about drainage, i saw a neighboring house have a PVC pipe coming down the side of it carrying water from the top down to street. lol idk

Super clean, really well maintained and needs next to nothing.

While I don't particularly mind what I do, I certainly don't see myself doing it forever and view REI has a solid, long-term option to create other income streams for myself and a option I can start out in while maintaining my current job.