If you are serious about learning how to rig, get the Gnomon Workshop or Digital Tutors DVD's. If you have tried rigging and can't grasp it, the videos will go over everything you need to know. It sounds like you're struggling with some fundamental concepts so you need some expansive and fundamental answers, unfortunately…
I SUCK at rigging. Plain and simple. I use maya 2008 and I have watched the DT training video at least 3-4 times and my characters never work. My clusters always disappear when I delete history (as the video says), joints will not deform properly even though I have oriented (spelling?) them, paint weights to verts for…