"How can I sync my T-Mobile G1 Google Android phone with my Outlook contacts and calendar automatically?"
Knowing that Google provides a great free solution for syncing Outlook with Google Calendar automatically, I was extremely hopeful they had finally offered a solid solution for managing contacts between Outlook and Gmail. So far, Google's only automatic solution involves syncing Outlook with iTunes, which is great if you have an iPhone, but kind of inconvenient for an Android phone, especially since you need an iPod for it to work. After trying several of the free solutions, including GCalDaemon, which acts as a local server for your contacts, I concluded I'd rather pay for the reliability of an app I'd recommended in the past, CompanionLink.
Back when I first looked for solutions to sync Google Calendar with Outlook, CompanionLink presented itself as a highly reliable solution. When Google released a competing tool for calendar sync, it no longer made sense to recommend a pay product, so I stopped recommending CompanionLink. Now that there's a need for a reliable contact sync solution for the T-Mobile G1 Android phone, CompanionLink is back at the top of my list.
Here's how it works: You install CompanionLink on the computer running Outlook. Provide CompanionLink with your Google sign in info. Choose the settings you want to synchronize and the frequency. CompanionLink handles all the details of keeping both calendars and contacts in sync. The phone part of the equation is easy, simply provide your T-Mobile G1 phone with your Google account information and all the data that's synced between Outlook, Gmail, and Google Calendar will be available on your Android phone too.
As far as I can tell both CompanionLink for Google and CompanionLink for Google Android do exactly the same thing, which is to sync your Google Account with Outlook. The Android part is handled entirely by Google. Another app I considered was OggSync, but I opted for CompanionLink because OggSync has an annual fee and CompanionLink is a one-time purchase.
For getting your mail sync'd up, you need to follow a few steps to import old Outlook mail into Gmail.