Send a letter start the communications.  

I lost my premier host standing because I had to initiate a cancellation and despite having all of the communication in writing VRBO wouldn't credit it.

I don’t want to mess around with homeowner grade stuff from Lowe’s or whatnot, and am willing to pay a fair amount to start getting these under control  professionally. 

Look for similar properties nearby on Vrbo and Airbnb to see how they are doing to see how this might fair as a STR.

The issue I face is the guest house is fairly small but fine for a single individual.

Are there any resources that exist to determine what the fair market price for a condo should be in a particular area?   

4) What will be your screening requirements to comply with Fair Housing & local statutes?

That's what I think a fair price is.It does depend on how far it is to the roofing supply store, how far it is for the workers to travel, if there's any rotting wood that needs to be replaced and how busy they are (busier = higher profit).You could buy a couple ladders, a compressor, a 100ft extension cord (14/3), 50 ft of rubber air hose, a roofing nail gun, a caulk tube a couple shingle removers and pick up some day laborers who know how to roof. 

You've probably heard of big Landlords losing property, but only because they were flagrantly violating Fair Housing, running a slum, or otherwise violating the law in an egregious manner.

Escrow companies that are responsive and communicate well.