@Lara Nicole Since I am not currently investing in the area, I cannot offer any real data to back up my opinion. Still, just my two cents: I see the demand and appreciation for SFH steadily increasing in the future. Like others have mentioned, Portland is located in an interesting region geographically, between several major west coast cities: Seattle, San Francisco, and LA.
Regardless of the wacky laws and lack of law enforcement, people will still want to move here. The kind of people attracted by those stipulations is a whole other conversation. Not to get political, but many of the things you mentioned (homelessness, increase in crime, and the overall lawlessness) can be traced back to the people running the show here in Portland, who are voted in by people who live here. So, in my opinion, these things kind of feed off each other.
I personally moved to Portland because I, like many others, appreciate the natural beauty and landscape of the PNW. I want to be within arms reach of the beach, mountains, and forest. However, I came to learn very quickly that there is a lot of pros and cons to living and/or investing here.
With that being said, I cannot see myself staying here long-term; however, I do see Portland increasing in value and appreciation over the next several years. As others have mentioned, Portland is surrounded by protected land, so we really do not have an opportunity to continue sprawling outward like LA. Portland is also a unique location that tons of people will continue to visit (at least I hope so).
Investing in the suburbs surrounding Portland may be your best bet (Gresham, Tigard, Beaverton, etc.) since these locations tend to attract a different crowd than the downtown crowd if you know what I’m saying. Brandon Turner said on one of his webinars that he always asks himself before investing in a specific location if he feels comfortable with his wife running alone outside at night. The point being, would you feel safe walking around the neighborhood you’re about to invest in at night by yourself?
I hope this can provide you with another perspective. Again, just my two cents!
-Ben