If the repairs are strictly cosmetic and less than $30k you can do a 203K streamline loan, spend the money on things like kitchens and baths and focus on transitional design that will stand the test of time.

My intention is to transition from contracting to investing.

Good luck on the transition!

We transitioned back to this for a couple of years during the Great Recession.

But my biggest worry was that Oregon isn't too landlord friendly so I just wanna make sure all bases are covered to mitigate any other headaches that may occur during the transition.

Situation:I currently have 20 units in my home state. I am moving back and taking over management of my properties in 3 months. I've owned rental properties and have slowly grown my portfolio over the last 20 years.  ...

I don't really know how this transition works for month to month leases.

Plus, a lot of the non-gentrified neighborhoods are now places that are much further out, or lack good transit access, unlike Bed-Stuy, which is close-in, has good access, and has beautiful architecture that appeals to rich people.  

The only way I've learned to do that is by buying cheap in transitioning neighborhoods and self managing.

I’d suggest networking with those that are in the same field and have transitioned to being a REI, they most likely will have the same concerns you had.Lastly, ask your 401K Admin if you are allowed to roll VESTED dollars into a “Self Directed 401K”, you can google it and get a ton of FAQ.