If you set up a personal e-mail account (for example:hotmail.com) with the second icon that says "Personal email set up" on your work blackberry, do those emails go to the work server even though it goes through internet to connect to the hotmail.com site?

if you send it no but if you recieve it yes

Keep in mind, too, that your work BES can limit your ability to send 'as' the personal account, or can block your receiving them altogether.

Might want to touch base with the BES Admin to find out how the IT Policy is set up.