regarding topography; portland, inside the city limits has over 1000' of elevation difference (so there are plenty of steep streets here as well, and landslides if that is what gets you going. this also helps create micro-climates, so yesterday morning my yard/house/street was covered in ice, but just a couple miles away at amy's, totally above freezing) Mt. Tabor is an extinct volcano caldera that sits well inside the city limits. portland is home to one of the nations biggest urban parks and is (?) the largest urban forested park. we sit at the confluence of only 2 rivers, so 3 beats 2, but the columbia is longer than the ohio and monongahela combined. portland is about an hour from the ocean, mountains (higher than anything in PA) high desert, and a massive gorge.
i've always thought pittsburgh seems like a fascinating city. and it looks beautiful. and there are metal bands from pittsburgh that i used to love (CIC, willowtip stuff).
debating the natural topography is fucking stupid. debating what city is more bike friendly makes more sense. and portland for now is unbeatable in this debate. as far as pussy weather, sure. portland isn't set up to deal with snow as it's not a standard feature of winter. ice is what we deal with mostly. but the city doesn't salt the roads (that shit isn't good for the water and soil). so it gets icy and everything stops.
the only other thing i can think to mention is that portlanders are only as soft as the places that everyone moves from. meaning, no one is from here. i know 5 people from pittsburgh, no idea how many from mpls, illinois, california, mass., texas, DC, etc.
take it easy, keep biking.