Colorado to Philadelphia With Family

Hello everyone and my hopefully-soon-to-be neighbors!
My family and I are looking to move to Philadelphia in late summer/very early fall of next year for education related reasons. We are hoping to live in or as close to Glenside as possible, as doing so would allow us to be a 1 car family.
My wife and I have been Coloradans our whole lives, both of us grew up in the Denver metro, and we’re living in Colorado Springs at the moment with 2 young kiddos and 1 on the way.
I love Colorado, and will miss it. CO Springs a bit less.. they’ve privatized everything so we can’t affordably take our children to the pool in summer, the PT is laughable, and we just had our utility rates spiked while approving a data center in the span of a summer. Everything I’ve read about Philadelphia makes me excited, and I think it’ll be a nice place for us to live for at least a few years.
I’m curious to know what we should expect about anything and everything: cultural differences, how much winter is going to kick my butt, your favorite thing about living in Philly, experiences from people who moved from CO, etc.
We’ll also be visiting in the Glenside area mid-October, so I’d also love to know what a good place for a cheesesteak would be.