Ha, that's a coincidence... I just had to do this for my mom because she syncs both her and my father's blackberry's up to the same laptop and didn't want the contacts to mingle in the same address book. I had to create multiple profiles for each phone to sync to in outlook. I'm assuming this will also work if you're just trying to sync the same phone to different profiles as well.
It's pretty simple actually, but just as always I had to go and make things difficult. I found a
website that detailed the process.
To give you a brief overview of what I did that was extra, I'll explain it a little bit.
1.) I actually deleted all the old pst files (personal folders) from their default location (C:\Documents and Settings\UserName\Local Settings\Application Data\Microsoft\Outlook).
2.) I deleted all profiles/accounts from outlook by going to Control Panel>Show Profiles>Remove any Profiles.
3.) I added the new profiles (ie. Marsha/Sam but in your case it would be Work/Personal)
4.) Select view or change existing e-mail accounts, then click "New Outlook Data File" this is where you create the data file to contain either your work or your personal info according to the profile you just made (ie Work.pst).
5.) Rename Personal Folders to the same title as the pst file (ie Work)
I think this should be it... then you do the same thing for the other profile starting at #3 and you now have 2 profiles, just make sure you've selected "Prompt for a profile to be used" that way each time you connect your phone, outlook will ask you which profile you want to sync to. The reason I deleted the old pst files was because I wanted to start fresh the first time I synced each phone. In your case I'm not sure how to have more than one calendar on one device itself, but I know you can sync to 2 or more different calendars by creating multiple profiles.