This is typically due to a high principal and low median rent within the area or its remote and I believe it may be a struggle to find tenants.

I worked for a family office in an acquisitions role specializing in sale-leaseback transactions.

And I'd highly recommend doing a once-per-year walkthrough of the property yourself, so you know the manager is working in your best interest. 

I am worried about getting in with the prices being so high in the entire Portland area, but I’m more worried about not getting in and getting my real estate portfolio going.Best Regards,Justin

I highly recommend finding some events to go to on meetups.com/Facebook/your local REIA website.

Any recommendations from out-of-state investors like myself would be highly highly appreciated.

The issue, of course, is that renting close to a college/university is highly seasonal in that students want housing mostly for the beginning of the fall semester. 

The house itself looks like a very nice acquisition and in great shape, so you did good there.

I’ve been spending time there since I was a child and it feels like a great place, (except for the high crime and drug use, areas which I would never invest in…).

There is some accounting included, like owner statements and keeping track of all the important numbers for a STR property...i.e. occupancy, revenue, RevPAR, etc.As for guidebooks I highly recommend going on Etsy and finding templates for hard copies and templates for a digital copy.