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

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

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

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. 

We've got a chat tool on the site, but no one to organize the chats right now.

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…).

If you can't keep control of your personal finances, you are highly unlikely to succeed in real estate investing.

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.

Many of your recreational campgrounds are owned by the government (either state or local) and almost all of them do not allow you to stay more than 21 days so if you are running a long term park there is a very high demand in many states. 

We usually don't analyze residential properties (1-4) with Cap Rate...but your price points are quite high, so maybe those are 5+ units?...