2) There should be a "Mobile Favorites" under your IE's Favorites list. You could bookmark some sites into there, checkmark "Make Available for Offline Viewing". There should be some customization options available there or after adding the site that allow you to schedule the webpage synchronizing or doing it manually. I haven't actually tried this, but you could give it a go

3) I don't know. Don't have an iPAQ.
4) Don't know either. My devices are not supported for WM2003.
5) Don't know this either. Haven't had this kind of problem.
JJB