[jasonbvr]

Yeah, the actual worth of having the JR pass depends on how many long distance trips you are making. So Samokan's question about if you are just going Osaka-Kyoto-Tokyo is really important.

Taking the night bus, you don't exactly lose that much time because you are on it at night. If sleeping in a seated position isn't a problem (which is true for like 99% of Japanese), you will be fine. The cheapest night buses are those that go Osaka-Tokyo on the weekdays.