I have just done this with my new G2 and this is the route I would recommend.
Export your outlook contacts as a CSV file.
Logon to gmail and import those contacts.
Sync your G2 with gmail and it will import all your contacts.
The reason I wouldn't use HTC Sync is that is add a lot of tasks to windows you really shouldn't need running all the time and also there is a good chance it will delete your contacts from Outlook as it did on mine.
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