I have been refraining from posting here up until now, but I can provide firsthand observations of the state of things in Portland. And I do mean firsthand, because it just so happens that a solid majority of the protest sites here are either clients or closely adjacent to clients of the private security company I work for.
1. There has been a surprisingly sharp and clearcut distinction between the protests and rallies during the evening, which have been completely peaceful, and the protests that happen after nightfall, which have been more militant. The daytime protests have continued to happen every single day since the Floyd killings. The nighttime protests were initially also every single night, but have tapered off somewhat and in the past couple of weeks have happened mostly on Friday-Saturday-Sunday nights.
2. More militant is still very relative. The vast majority of the more aggressive protests are only "present and shouting", with a handful of people throwing things (mostly fruit, water bottles) at the police or trying to knock down barriers.
3. Smashing of storefront glass and looting *did* happen, but it *only* happened on the first two nights and has not been repeated since. The looting was confined to a very small number of stores in the downtown area; the only widespread vandalism has been tagging things with spray paint.