I'm in the unenviable situation of being asked to migrate a mail server from Exchange 5.5 to Exchange 2010. The domain has two sites connected via T1 and an exchange 5.5 server (neither are installed on DCs). I know there is no direct path from 5.5 to 2010 so I've been working on trying to migrate to an Exchange 2003 VM first before migrating to 2010, but it's been hellish.
The domain only has about 150 users, I'm wondering if it's worth it to fight through this or to simply stand up a new mail server and manually recreate accounts, public folders, and calendars. Maybe, I can even export the calendars and recreate them, since they're fairly important. If I can convince the users to backup their entire mail box to PSTs, I think I can add them to a configuration in Postini that will push their mail to the new exchange server. I feel if we do this in small batches it won't be a complete disaster. Anyone have any thoughts on this? I'm not married to the idea, so I was hoping someone would be willing to either poke holes in it or give me some extra information with which to work. Thanks.