All of this is extremely helpful. The problems I was/am having are:
Watching my feet, and I have a hard time telling myself I can "make the gap" in my head. Ollie-ing itself is difficult for me... I have a lot of heel lifting in my boots...
dont worry if you cant actually ollie onto it. A simple hop works fine. Making the gap comes down to comitting to it, once you look at that feature and decide to hit it dont start second guessing yourself or thinking about what ifs, just do it as focused and as best you can. Looking down at your feet, just dont. Make sure you watch the end of the rail. In boarding if you look somewhere thats where you are going to go, so if you look at the end/beyond the end of the rail your body will begin to make the little movements and adjustments you need to keep you there.