It literally blows me away to see the price per square foot in some areas compared to a couple of years ago.

If there's only 50sq foot of absorption area, that sounds like a one bedroom house.

I feel as house hacking a SFH will provide me all the control, responsibility, and flexibility I need to really get my foot in the door with REI.

as screwed up as Portland is politically.. the RE market like many areas is quite robust to red hot.. 

its a robust sellers market in many areas of the country.. 

I even live on a street that has a lot of vagrant foot traffic, a sometimes occupied abandoned house behind me and my girlfriend works from home.

This includes upwards of a dozen 4 foot wide rolls of torn carpet and subfloor.

That being said, we are still seeing similar percentages in property tax out here in the much less densely populated west Texas where rent per square foot is quite a bit lower and are still cash flowing.

Frankly, there are many here that feel that Amazon has one foot out the door.

This past year I spent acquiring a variance from the town ZBA to be able to reconstruct in the same foot print and rebuild a 2 family.