Looking for a place to live

Hey! My boyfriend (28) and I (24) want to move from Texas all the way to Pittsburgh. I have checked out a few of the recommended places to live in this sub, but I am wondering what area would be best suitable for our little family! We have no kids and two cats. We both work in the service industry (bartender/barista) and currently pay $900/mo. Rent here in Texas for a two bedroom house. Any area with rentals under $1500 would be preferable at least until we get settled. As far as interests, I love to be outside and appreciate a great park (even better if it’s a skate park) we enjoy nightlife and currently live on historic Route 66 so an area with rich history would be preferred as well! We both have vehicles but would prefer a walkable area.

Thank you for any help and advice!