I had a relative show the house for the first time in 2018, and have remotely managed everything from day one, from 5000 miles and 7 time zones away.

If often more that they are abandanoning the property to the government because there is some type of constraint, i.e. there is a street light oddly placed in the middle front part of the parcel, there is a creek or wash (which means environmental permits would be needed), there is lack of true legal access, zoning problems, etc. 

It's important to understand their reputation in the industry and the market, as well as any potential risks or red flags.Knowing your client's objective is also crucial.

Recent repeat flooding, even thought outside of FEMA flood zone.

Most likely not depending on zoning.

Brookings OR - There is a specific zoning code that investors can reliably obtain a permit with the city.

This is an immediate red flag.

Applicants offering to pay extra are a red flag.

The current regs pretty much don't allow NOO STRs to be operated in any residential zoning.

Also, any insights on how hard it is to get a zoning change approved to make this a legal 3 flat?