What Pocket PC are you using? Until Toshiba released EUU3 (End User Update 3) for the e740, I wasn't able to log into many secure sites, Hotmail included. Most Pocket PC 2002 devices should have no trouble logging into Hotmail by going to
this page and clicking the Hotmail link. That will take you to the Microsoft Passport login page. Log in there, and you should end up in the mobile version of your Hotmail mailbox.
If that doesn't work, please post back with some more details about your setup. (i.e., what Pocket PC, how you are connecting to the Internet via your Pocket PC, etc.)
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Dave