The level of syncing you're looking for is generally reserved for BES, not the BIS you're using. There are hosted solutions for BES, available in the forum marketplace BlackBerryForums.com Sponsors - BlackBerry Forums Support Community
It adds additional costs to your plan, but it's worth it if you absolutely need syncing. I have a MobileMe email account on my BlackBerry and it works very well. Sent items from my BlackBerry appear in my Sent folder in Mail.app on my Mac, but that doesn't happen with every email account. Email providers like Apple and Google have been upgrading so some of these syncing features work with BIS, and Yahoo mail has augmented BIS integration as well. It *should* work for these accounts with Outlook, but the accounts have to be set up as iMAP accounts on your pc.