Need Help: Osaka-Tokyo using JR Pass

Hi Daniel

I just need some help with my itinerary. I'll be traveling to Japan this Dec 8-15 via Narita. My friends and I will stay in Tokyo for 4 days and they will fly back to Phils on the 12th leaving me alone while I embark and explore Osaka and probably Kyoto until the 15th. Our itinerary in Tokyo includes trips to Disneyland, Hakone and Gotenba.

I initially planned on just spending my 3 days to visit the Universal Studios as well as other tourists spots in Osaka, but due to a friend's suggestion he wanted me to explore Kyoto as well. I am planning on purchasing a JR pass and my dilemma is this: My flight back home is on Dec 15 12:20pm via Tokyo and I intend to stay in Osaka up until that day to maximize my stay.

I've done a little research and the earliest available trip from Osaka to Tokyo via shinkansen is 8am. It wil be impossible for me to catch my flight by then. That leaves me to my only option: Trying my luck in using Japan's night train that is available to use for JR pass holders. It will leave Osaka at 12am and will arrive in Tokyo at 8 am just in time for my flight. Do u think it's a good idea? Have you tried it before? I've read somewhere that it doesn't provide reservations so it will be a bit risky to try it. Can u suggest any other means?

Also, is the JR Pass worth it in my itinerary? Can I somehow use it while I explore Kyoto, Osaka, and USJ?

Thank you very much. Looking forward in hearing from you soon. 😀

Belle