This video sums it up perfectly, and I am not kidding.
Basically, you should just watch the show. It is full of Portland-as-a-main-character-not-just-a-backdrop in almost every skit. Is that always funny? No, but no one can be funny all the time. You probably won’t get all the jokes, and that is okay – because that too is ‘very Portland’ in a non-threatening or mean way!
For Where I’m from (part I), look here, or you could also look here, here, here or there…because I love Portland, but it is totally like a cult (you can never truly leave – even if leaving was the most Portland thing my husband and I ever did)!