This thread is for people who want a fully automatic way to keep both Calendar & Contacts sync'd both ways between Outlook and Google Gmail / Calendar.
I've already done a lot of research on this topic as it is currently the most important item I've got to have working in order to keep the Droid. It seems like nobody really has a great solution yet, but there are some in the works. This thread can serve as a master list for Outlook sync software.
Here is what I've found so far:
CompanionLink $40 (released, sounds like the best currently available): Sync Microsoft Outlook with your Google account and your phone | CompanionLink
Missing-Sync $40(update: Released. Calendar syncing is now supported, but requires additional app installed on phone.
): Keep your life in sync with The Missing Sync for Android from Mark/Space
Appears to be the best all-in-one solution for syncing Calendar, Contacts, Notes, Docs, Media and more. Includes 'Proximity Sync' - syncs wirelessly & automatically w/ your computer.
gSyncit $15 (released, but lots of problems reported by users. EDIT: Some favorable reviews in this thread, may have improved reliability): http://www.daveswebsite.com/software/gsync/
SyncMyCal $25 (released): Share Outlook Calendar Free, Google Calendar Sync, Pocket Outlook Google Sync - SyncMyCal
Anybody using this?
OGG Sync $30/yr (Not yet released): OggSync - Sync Google Calendar and Contacts with Outlook and Windows Mobile Device Sync (including Microsoft Office) Blog Archive Real… Native… Google Contact Sync — OggSync 4.0
Google Apps Sync for Microsoft Outlook $50/yr (Requires Google Apps Premier or EDU Edition): https://tools.google.com/dlpage/gappssync
Know of any others? Are there any good free apps out there that can sync Contacts? Tell me and I'll add them to the list.