Coming from Windows Mobile OS, I completely understand what you are looking for as I am in the same boat. I'll tell you what I am doing and what I've found. I went the CompanionLink route. The program has come a long way since its first release and I expect some good things to come in the future. Its not a complete duplication of the sync that we are used to, but it will do. I use CL and a USB sync for the contact information only. I am allowing Google to handle the calendar as there isn't much there that I would be of much value to anyone. The one thing that I have not seen a good solution for is the Outlook Inbox being duplicated to the Droid Inbox when doing the USB sync. I have my e-mail accounts set up as IMAP and get live mail messages off of the servers, but I'm missing the stuff that is already in my Outlook. I should also clarify that I do not use Exchange. It is strictly a standalone system. I have come to accept that this is a shortcoming of the Droid and the OS and really like the phone enough that I will accept the workaround in the form that it is. Yes, we may wish to be doing things in an old fashioned manner, but there is hope that CL will eventually come pretty close to what we need. I doubt I've helped except to offer my own experiences to you.