2) Times are always off in mail messages and/or calendar events. How can this be fixed?
First, go to the Date & Time preferences, located in:
OS X System Preferences: Date & Time
OS 9 Control Panels -> Date & Time
First, check to make sure the city listed is in the same time zone as your computer. If not, change it to a city that is. You may notice that the time has changed accordingly. Change it back to the local time. Official time can be found at the U.S. Time Service within the U.S. or the World Time Server for non-domestic locations. There is also information there on syncing your computer clock to their time server, to always keep your clock accurate to the official time.
Now, if you have Entourage 2001, you are done. In Entourage X, go back into Entourage and go to Entourage -> General Preferences. Under the Calendar tab, choose the correct time zone.