There are a lot of roofers, not as many flat roofers and really not as many that are licensed in the city with insurance.  

Quote from @JD Martin: Quote from @Jay Hinrichs: Quote from @Matthew Drouin: Small wine town is all I needed to hear.Seasonal tourism is usually not a great industry in which to build a sustainable business.There are probably higher and better uses of your capital near high velocity metro areas.We have small wine towns near our city in the finger lakes region of western NY.  

My city does allow month to month rental.

You're not going to know the whole city from one visit but you may be able to identify and drive one or two strong "buy" locations for yourself.Best of luck!

If any of your properties are discovered by City officials to be unregistered, you can receive an administrative citation for failure to register; this penalty can cost $100 or more per property.

I have tons of connections with people who do marketing all over the city I live in.

Maybe every city is like that, but for me more than almost any other city I have been too I think you really have to know the area and have to know the tenant base. 

But ideally you don't tell us, you are just going to have agents pitch their city like @Julian De la Guardia & the sort.

The city came out and determined that the problem was actually on the city property, and not ours (the tree was outside our property line and so were the cracks in the pipes.)

/city regulations, set up costs, doing things to stand out) and leave you with less cash in case of an emergency.