Hey Aaron,
I second the frontroll suggestion.
Regarding the Raileys - are you trying them unhooked or hooked in? This ties into the load and pop thread and Warren's suggestion of testing the water with unhooked riding:
I've found that after years of riding in the default upwind position all the time it becomes very difficult to convince yourself to flatten the board off and ride straight downwind towards the kite. In my mind's eye, when I do it, I'm going miles downwind, even if I only let the edge off for a second - but in reality, for a very long time, I wasn't going towards the kite nearly long enough.
It's really important to do this though, if you want to get a good load and pop. When you ride downwind, the kite moves deeper into the window (i.e. more to the front of you and away from the side) and the lines slacken a bit. Then, when you carve away, like in a backroll, you'll get a really big spring: with the kite deeper in the window, it's more in the powerzone and when you carve when it's there, you're pushing the board directly against the pull of the kite.
You need to ride towards the kite for at least two or three metres though - which takes longer than you think!!! Try counting one-onethousand, two-onethousand, three-POP!
If you can get this big load and pop, front rolls will be a lot easier as you'll have a lot more time in the air. (everything becomes easier actually)
This also ties into unhooking and Raileys, because for years, I was only releasing my edge a little bit, unhooking, and then trying to edge against the kite - killing my hands and arms after only a few short seconds - and scaring the bejaysus out of myself in the process because of all the power.
Flatten the board and ride towards the kite and you'll hold on no bother at all. When you carve, drop back deep and stomp the board - you'll spring up and the pull through your arms will drop as soon as you're in the air. Whether doing Raileys hooked in or unhooked, with the right pop (hooked in you have to pull the bar hard too), you'll have no issue getting your legs up behind you - they'll go most of the way themselves. The harder you pop, the higher they'll go.
Whether you Pop on three or count 1,2,3 and then Pop is an ecumenical matter.