I'm from "nowhere" as well (military brat), and I agree with him completely.
Pittsburgh isn't "charming" or "quaint" or "cosy"... it's stinking s**thole.
Compare:
Pittsburgh, PA is the 22nd most populous area in the US.
Portland, OR is the 23rd largest.
In Pittsburgh, if you want to get from point A to point B using public transportation, the ride (one way, staying inside one zone) will cost $2.00. The usual wait time for a bus is 10+ minutes, as the buses rarely follow the schedules closely (as such, if you do not wish to miss your bus, you should show up 10 minutes before the scheduled arrival time).
In Portland, if you want to get from point A to point B using public transportation, the ride will cost you $2.05. For that $2.05, you can ride all you want in one zone, on any form of transportation (rail or bus), for two hours. You can ride all day, all zones for $4.75. All forms of transportation show up close to the scheduled times, and the light rail will inform you of any delays (depending on the stop).
In Pittsburgh, if you choose biking as your main form of transportation: pray. When the weather is snowy or icy, you may as well not try. Nobody shovels or treats their walks and the roads are just too precarious to attempt. Pittsburgh drivers do not know the law pertaining to cyclists and will either buzz you, pass on a double-yellow, turn in front of you, or yell at you for just being on the road: all of which is technically illegal, but the city cops don't enforce the traffic laws. Seeing drivers run red lights, turn on 'no turn on red' intersections, and turn without signalling are all commonplace. This is not surprising, since, to get licensed in the state of Pennsylvania, you need only answer 13 of 15 questions correctly and pass a standard, 10 minute on-the-road test. Also, on any given stretch of well-traveled road, you can find at least one dangerous pothole.
In Portland, if you choose to bike, despite the fantastic public transportation, you will have bike lanes and drivers who will respect your right to the road (for the most part). The weather, even in winter, is usually pleasant, if rainy. It rarely snows. Portland cops enforce the traffic laws, even for cyclists. Oregon is well-known for having some of the most difficult driver's tests in the US. In fact, even as a pedestrian, if you approach a crosswalk, traffic will stop automatically until you get across. I'm serious. I've tried waving them on... they don't go until you're across. Finally, the entire time I was in Portland, I didn't see a single pothole.... but maybe I wasn't looking hard enough.
Can anyone give me a good reason why Portland works and Pittsburgh doesn't?
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