This is interesting, two truth-orthogonal comments.

As someone who has never been to the city - not 20, 10, or 0 years ago - how should I go about verifying which one is "more true"?

Both can be true. Portland has some nasty parts (inner downtown, anywhere near a trail or a body of water) that are riddled with needles or feces, but there are also some very nice parts like the suburbs or anywhere that can afford private security.

I live just outside Portland, and the homeless problem is MUCH worse here than it was 10 years ago. For one more data point....

My quick hack for plausibly quantifiable info is to do a google image search and scan through the charts to find a trend.

Take a guess.

For my own clarity: Do you intend more of a "flip a coin" meaning or more of a "we should inherently already know what the answer is" meaning?

My density today is more than average.

I don’t know if that last bit is completely true. Portland was worse on my last visit earlier this year than it was on my first visit almost ten years ago. On the other hand, my wife grew up in Oregon and from her account, the city was dirty and full of drug addicts when she was growing up in the 1990s.