Well my friend is the one who has done all the arrangements =P. I'm generally just following her plan. However, I think the idea is that when we get to Osaka is that I'm probably going to just fall asleep since it'll probably be 8-9 pm by the time I get there and I'll be exhausted from the trip (flying out of Indianapolis around 5:20 am) =P. She had some other plans while we were in Osaka as well (probably take in some temples, since they're cheap), but those are the general areas we will be in on those dates. We mainly wanted to get there for Universal Studios which is on the 3rd, so it's just easier to get to Osaka first and then head to Kyoto rather than having to switch back and forth.
Anyway, seems like the e-pass would be more convenient and save me some money overall, but, as you say, limits where we could go and if we decided to go elsewhere might cost me extra over just getting a JR Pass. I do have a question about that though
I thought I could get the exchange order for the Pass mailed to me, but it seems like I would actually have to pick it up in the airport. However, it seems like I have to be a part of a certain group flight (JAL or ANA), and I'm not entirely sure how to do check that. I would be totally fine with just picking up a pass while in the airport (as it says I can do), but not sure if I would actually be able to do that since I don't know if I'm JAL or ANA. Would those flights have to have been tickets I bought from JR, or is there another way I can tell?