Outlook stores the contacts in a file with wab extension (could it be Windows Address Book?), so the simplest solution is to export your contacts under Windows, reboot, locate that file and import it under Thunderbird, Evolution, or the mail client of your choice. Maybe there already is a file storing your contacts, "hidden" somewhere under your Documents and Settings\<username>\ folder, but I don't remember properly.
This method, anyway, does not propagate the changes you make to your contact list (under Ubuntu) to Windows, since it could be seen as a simple file copy operation. And I don't know how to keep them in sync. Maybe you can do something of the sort using Thunderbird both in Windows and Ubuntu, and making Thunderbird under Ubuntu use the same profile folder used by Thunderbird under Windows. Anyway, I don't know how much is this advisable.
For the modelling application, I can't help you, I'm sorry.
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