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!

In short, my membership fee bootstrapped me such that I have more than doubling my net-worth. 

Start by leveraging what you already have—consider tapping into equity through a HELOC, house hacking again with an FHA loan, or increasing cash flow by converting a unit to a short-term rental.

The bullet in the response that is standing out to me is:"(7) The accessory dwelling shall not be a short-term residential rental, as defined by City Code section 3-2-152(a)(2), for a period exceeding 120 days per calendar year."

With the fires, labor and materials are going to be in short supply.

BTW - AirBNB is a platform where you list your Short Term Rental.

I just did one for like 28k, was a little short on a closing cash purchase. 

In 2019, I launched my own revenue management agency to help Airbnb owners boost their income and achieve greater returns on their short-term rental properties.

But neither do you, yet you started with:"Short answer is "yes"  - which I consider misleading.And you manipulated the OP's question to fit your agenda.

Currently, we manage approximately 40 short- and mid-term rentals, in addition to a few long-term properties.