Sync setup question: will Android, Outlook 2010, Gmail, calendar and contacts sync?
Android syncs to Gmail, Contacts, and Calendar nearly effortlessly. It seems like in your case it's Outlook that is the problem child. Do you need to sync contacts with Outlook too? If not, a one-time export/import from Outlook to Gmail should meet your needs.

I would say have Outlook sync with Google and have the phone sync with Google. Syncing the phone to Outlook too will probably duplicate data and/or leave gaps in your data.