How do you conclude that Philadelphia is a much more interesting and hip city when compared to Pittsburgh/Boston?

I can't speak to Boston, but having lived in Philadelphia, Pittsburgh and a suburb of NY (Fairfield county CT), Pittsburgh has the most accessible cultural outlets. The local art scene is incredible, there is a top tier orchestra, the city is mostly bikable (with more protected bike lanes on the way), there are 3 professional sports teams that are within 20 minutes on public transportation of anywhere in the city. The list goes on. There may be more things to do in NYC than Pittsburgh, but I constantly felt like I had to pick and choose because it was just so expensive.