It's a nice place but in a small town it can be tough to find a good property manager.

Consider different strategies like mid and short term rentals as I believe the Portland area would allow for success in both (although I have heard Portland proper is tough on STRs).Best of luck!

Often times, they are priced at market and makes it tough to get deals done with agents.

Hmmm this is a tough one.

As others have stated, you are far better off working with an experienced Broker that can navigate for you during these tough times. 

And doing 3-4 units FHA is tough unless you have a huge down payment. 

After years and years of being frustrated by how tough it is to find honest, communicative contractors, I decided to start a Handyman/contracting business.This is NOT a solicitation.My question is – What are Property Managers / STR Owners / Investors looking for when they need a handyman and how are they finding them?

It’s tough to know what is happening when you can’t get any responses! 

If you dont have the tools and skills to DIY and get yourself out of a tough spot then you can be SOL if the deal goes south.

Ask for higher security in person have them back out on their own if they still want the place you will be safer with more security