I did the exact same thing 5 years ago except it was a single family and I rented the rooms out to friends, now my wife and I have built a portfolio of 10 homes.

Out of town, especially in places that are tenant friendly or C/D areas, are for experienced investors only.

I'll be upfront- the nature of our interaction with our clients will also become more scale-friendly as we grow. 

Even though ALOT and I mean ALOT of people on bigger pockets or friends and family have told me airnbnb arbitrage wouldn't work out I have been pretty successful even though I was pretty much self learnt without any form of joining a course or anything like that.

If you are considering this approach, I suggest you buy an A-class property in a landlord friendly city and get a PM.

If you are really in Portland, you're going to have to really review the eviction requirements because it's known as a tenant-friendly locale. 

Excel is your friend as is your favorite 10B-II emulator app or even the 10B-II financial calculator itself!

I know only carpentry, but I have friends who are electricians and plumbers as well.

They keep rent low, give gifts and homemade cookies for Christmas, make upgrades whenever the tenant requests,  accept all the late rent excuses, etc.The truth is, your tenant is not your friend.

If he gets put out he's just going to wear out someone else's welcome, which is probably a friend or family member and that's where he belongs instead of putting off his problems on you.