[Capsyze]

yea when you have the sync box checked upon set up as you said you do it will check the server. however you have to go to your email settings for hotmail after initial set up to set how often it checks because initially it is set to manual meaning you have to tap send/receive to get emails.

Go to mail/ account settings/ options/ then click hotmail and change sync frequency to whatever you feel.
(sorry if im a little off ive been with the tp2 for a while now)

i always select as items arrive but if you want to have it set to check less often use a different setting (the less often if checks i would assume it uses less battery).