Even if it is just a walkaround and not measuring anything; the contractor should be there if you are new to this to give you an estimate.. 

Welcome to BP. 

Quote from @Ran Fridman: Hi, I'm Ran Fridman, I am a Property Manager in Indiana, Wisconsin and Illinois, for many successful years of servicing Happy Landlords and Tenants. 

Another example of this is the reduction in new construction starts for residential over the past 1-2 years.

I think you really need to work with an agent based on what I am reading between the lines in your post. 

Over the past two years, I've completed two primary residence renovations using 203K loans, created one LTR, one MTR, and now I'm excited to expand into flipping.I'm focusing on the Beaverton area and looking to connect with experienced investors who can recommend reliable lenders, wholesalers, or other deal finders.

the answers to all of your questions are... go find those people in person, which is difficult to do out of state unless you're traveling frequently to your chosen market. 

Initially rented to long-term tenants, it generated modest cash flow of a few hundred dollars a month with a 4.25% rate.

This person is unemployed but willing to pay 1 year rent up front to the PM company and sign a 12 month lease.

You might want to look up Ray Glymph on socials (Instagram).