Interesting thread. I've been thinking of doing the same thing a few years from now ever since last September when I flew with a guy with a steel
boat who painted it himself. He used a one part paint
that he rolled on with 4" wide foam rollers. He recommended rolling it vertically to avoid sags. He did not tip it, just thin coats with the rollers. He said it came out great and anytime he gets a scratch while cruising, he can get in his dinghy
and prep/repaint that area on a calm day in a nearly dust free environment
so a couple hours later nobody can tell there was ever a mark. After paying over $10K for an awlgrip paint
job several years ago, this sounds like an extremely sensible approach for a cruising boat to me.
I'm subscribing to this thread and will be interested in hearing how the OP's paint job comes out and any recommendations he has for painting, especially over Awlgrip.