Any input on decision making gratefully accepted!

There are a LOT of options for tootling around the east coast by rail, and a lot of people to try to see! I feel like I have a lot of time to play with, the pass is good through 5/16, but I won't actually be able to get everywhere...I'm thinking shoot up to Boston briefly, a few days in the NYC area, a few days in the DC area, maybe another day or two in Chicago and a couple of days in LA. I'd rather spend money on short train rides than hotel rooms, but not sure if that's practical. Like, there's an overnight route from NY to DC which seems like it would be convenient but it apparently involves sitting at the Philadelphia station for four hours. Is that something I want to do? Maybe! Should I be going to Philadelphia? Perhaps! Too many options.