RE: High end first?
Experience on planes doesn't translate over well to helis, and vice versa. Simulator experience helps tremendously for both, but you are still very likely to crash several times in the beginning.
I could fly nitro helis pretty well when I started with planes... I even soloed on my third flight/tank... but that was mainly due to my experience in the sim with planes. Still, I went through 2 planes in my first 20 solo flights, and crashed a few SPADs after that. If plane #1 was a $3000 gasser, that would have been a pretty painful entry into the hobby!