[SteveO86]

What you want to do is..

1. Add all your email accounts to your BlackBerry.
2. Under Options -> Advanced Options -> Default Services, make sure the default services are set to your desired email address.

3. Configure Outlook the way you want..
4. I would configure your contacts and calendar in 1 place first (outlook) - Meaning add all your entries in.
5. Once you data is in Outlook, then I would sync Outlook with the Desktop manager.

You will retain a single address book in Outlook, and your BlackBerry will synchronize the contacts will Outlook, keeping 1 identical address book across 2 devices (your computer and BlackBerry)

By default you will also be synchronizing a single calendar.
(multiple calendars will exist on your device due to multiple email accounts, but desktop manager will only the calendar set as default, under default services.)

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If you currently have multiple address books on your device, meaning you open your address books, hit the menu key and choose options and under "address books" you have multiple listings.

I would then recreate all your contacts in Outlook, then clear the address book database. (Desktop Manager -> backup/restore -> Advanced, select address book all and hit clear. I would also do a manual backup prior incase you miss anything)

Then sync you BlackBerry with Outlook, if all you contacts are in Outlook they will then be synch'ed back with your BlackBerry.
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Hope this helps a bit. Any questions post back.