And on another note, I am looking to get into REI to work for myself(freedom) and to create some wealth, nothing crazy if i could supplement my income and quit my job and work for myself i would be totally fine with that.

I am semi-retired and looking to supplement my retirement income with Real Estate and build a business that I can leave with my daughter and Grand Kids!

It can be someone who turned to investing as a stopgap or something they continued to do even after getting another job as supplemental income.

We are both now feeling pressure to supplement our incomes and we are choosing the real estate route.

Find a professional you can work with to supplement what you know, much like finding an attorney for a particular type of case within a certain jurisdiction.

I have also seen appraisers use a calculation based on the unit's rents and the area's average gross rent multiplier as a supplement to the comps. 

Or are you looking for a nice place in a great area and just want to supplement your income?

I was a police officer here for 18 years, doing investing on the side to supplement my future pension, but recently things have really started taking off and it overtook my full time job, both in time and pay, so I resigned and am now doing full time investing.My main strategies have been holding rentals, and more recently flips (with very extensive rehabs).

This makes it that much more important to supplement my income so I can be there for my family.

That being said I believe you can make money in the Portland area, you just need to be extremely picky and you'll definitely want to plan on having supplemental income.