If I couldn't get an iPhone, I'd get the G1. The iPhone screen is tough - and even tougher when you throw on one of those adheasive shields (which I recommend). I assume the G1 is similar construction. I only sometimes use a case for my iPhone, and it's holding up very well.
As to syncing with Outlook, there's always some cleaver soul coming up with a way to sync your phone with Outlook. I can't sync my iPhone with my work PC because those are locked down too hard for me to do so. So I just foward important scheduled items to my home Outlook and sync there (Go to the Scheduling tab under your appointment and type in your home e-mail address - wallah, it's now on your home PC too).