My leases clearly state that the "Tenant shall maintain all appliances, equipment, furniture, furnishings and other personal property included under this Lease". 

The scarcity of options that these people have makes them happy to drive a bit to solve their problem while also maintaining their comfort and safety during their stay.

Lenders often prioritize the person’s payment history hence it is imperative that you maintain proper financial records.Good luck!

An investor should always, "maintain to the neighborhood"!

On the surface it also sounds like you have a lot of local support for managing and maintaining the property but I suspect that will kill off most of the returns.The real information is somewhat hard to come by as the developer controls much of the market, the rental management, and a lot of the previous pricing data as they didn't report to MLS for much of their history.  

The property has a certain charm we'd like to maintain.

" * In addition to drying up investment in rental property, one of the worst effects of Rent Control is that it discourages property owners from maintaining and upgrading their property.

Most likely your STR will be well maintained at tip top condition.

The hope is that with poor MTR returns that various operators convert to LTR and the supply diminishes allowing us to raise our rates while maintaining a high occupancy rate. 

This way, I have direct access and communication with the landscaper and I make sure my lawn, trees, shrubbery, plants, and irrigation system are being well maintained.