What dongreerps said.
I teach from time to time, and tell my students (once they've learned the basics) to hook on to a racing crew list, and crew whenever asked (or just show up and look for a ride). Do what's asked, pay attention, and you'll get essentially free sailing lessons and free beer too.
I think your weather question will answer itself in due time. Don't go out looking for it, for it will find you eventually, and you'll learn from it when it comes. No sense intentionally rushing it, any more than you would rush emergency evasion maneuvers in a car (or whatever the equivalent is in an aircraft).
Sailing's easier than flying in this respect: if we manage to stall or otherwise screw up the wind flow over the airfoil, it only hurts our speed, while the ocean still holds us up. Not so for you aviators...;-)