@Kash Tacke I'm a big fan of ADU's in general especially here in the mid west, yes you could potentially be on the front of the wave, but housing density is the solution to the affordability issue, anytime you are investing with affordability in mind is a great strategy to me, and sound like there are some incentives or at least supporting winds form the local city, that in itself seems like it would be worth at least approaching an architect or contractor to bid up some plans or concepts to take tot he city.  

I would be self managing the property because I know the area well, have local connections to help out if in a pickle, and could get there in a day drive if need be. 

Network with other local investors and always have a solid emergency fund.2.

Also 4th quarter of last year Packwood and county officially did discuss potentially regulating STR's by either limiting numbers or adding a tax to cover increases in local services that are needed. 

A good host knows the local festival dates and has a handyman and multiple cleaners on call and ready to goa very clean house and quick turnaround are vital Im listed as a co-host but I pay a local host to do the legwork 

That said, be sure to check your local jurisdiction for other regulations.

All are local to me in a non-vacation rental spot.

You'll learn what contractors are good at such repairs, and eventually people will start bringing you "problem properties" with that issue.Another related idea: contact a good local realtor and ask them if they know of any on or off market properties that would be a hard sell for most buyers. 

You need to polish your skills, bigger pockets is a great place to start... find a local wholesaler you can work for/with and he will guide you. 

I also recommend a bank that has local branch that you can go into vs having it 100% online.