Here's a link to a post on the bottom painting job I did on my boat a few years ago which will answer many of your questions:
http://www.classicseacraft.com/commu...inting+project
If you're planning to leave the boat in the water for any length of time, I would seriously reconsider the use of Awlgrip below the waterline, since it's not recommended for that! The only urethanes I know of that will hold up below the waterline are Signature Finish and the stuff Island Trader used on his Moesly 21 (Insignia?). Signature Finish is intended for DIY type use (primarily brush, roller or roll & tip), so very easy to use, doesn't require any special primers, and can be ordered in any color you want, including all the standard Awlgrip colors.
As for how to paint the areas supported by boat stands, just figure out where you're going to put them while boat is still on trailer and then paint those spots before you pull boat off the trailer! Good luck with your project!