As far as i know, the only way to have "real-time" updates to outlook is through a BES or desktop redirector. there are two types, corporate BES and hosted BES. there's a whole thread dedicated to hosted BES. i'm not too familiar with desktop redirector so you'll have to do a search on that one. as far as the hosted BES, go here.....
http://www.blackberryforums.com/showthread.php?t=50
and you can go here for many of your other bb questions, or you might find things here that spark questions you didn't even know you had....hehe
http://www.blackberryforums.com/showthread.php?t=252