Should be no problem. You can point to any local port, and you can run multiple "kites" at the same time (assign public names to mupltiple ports at once). Just make sure your apps generate relative URLs and don't contain absolute IPs and ports and it should be smooth sailing.

Honestly, because I haven't yet taken the time to figure out how. Mostly that is because I have the feeling pip is more intended towards libraries and things used while programming python. Pagekite is not really a library (yet), it is more of a system utility, so integrating with the OS (rpm/deb and such things) seemed far more important.