I just went all through this issue myself last night and this morning. I was trying to sync outlook and google contacts. There is no easy way that I have found. If you enter a contact through the phone it is a phone contact type and doesn't sync with the google contacts. ??? Stupid if you ask me. And, the HTC Sync program is garbage. It duplicates all of your contacts and just doesn't work good at all. The best thing that I found was to export all of my contacts from both outlook and google into .CSV files. Then delete all contacts from both places. Then import both .CSV files back to google contacts. (this was easier than doing it through excel) Google contacts automatically formatted all the info from both files, and also merged quite a few of the matching contacts pretty nicely. And after that, it is very quick and easy to either merge duplicate contact info together or delete duplicates through google contacts interface. By the time I was done with the manual merge, the phone was already automatically synced to google. Tonight I will have to take back the newly exported google contacts .CSV file and import in into Outlook. Then I'll be in sync. It's just too bad there is nothing through google that will do this similar to the google calendar sync that works this well and is free!
Hope this helps.