Raleigh is pretty straightforward, all of his moves are in sets of 5 - that's the easiest way to remember it (for me at least).
He has 5 jumps and then he lands and is ready to be hit for damage.
Hitting him at the same time that he starts to jump back to his platform saves a little bit of time if you can time it correctly.
https://www.youtube.com/watch?v=jl5hDVihQb4&feature=youtu.be&t=2067
As normal, when you go back to load into the Safehouse - spam right and X until you get into the next area.