Start out learning to ollie OVER the rail (or try this with gap boxes). Once you are comfortable doing that go to some flat gap boxes and learn to ollie onto them from the side. Pretend like you cant just hop straight onto it. Once you are able to ollie/hop onto the box from the side take it back to the rails, starting out with somewhat flat rails that aren't kinked. Still making sure you are able to clear over the rail with out any issues then you just adjust your jump a bit so you land in the middle of your board on the rail vs going over it.
If you don't like the way I drive, stay off the sidewalk.
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do they even make chaps with asses?
I think they call them pants