As far as HoTMaiL and Outlook Express go, the constant user/pass prompting means that a server somewhere is down. I'd be willing to bet that you could go through the HoTMaiL web page and everything works fine there. Ever notice how OE tries to go to oe.hotmail.msn.com?
Anyhoo, Outlook (not Express) is the best e-mail+PIM program bar-none.
-SUO