I just spent about an hour with my next-door neighbor (the one who lives in the dorm room I lived in last year) trying to help him make Outlook work. It took two reinstalls, a downgrade, and poking around in the Control Panel.
Why? Outlook, when it gets a data file, believes that data file with all the zeal of a Southern Baptist bible-thumper. So when that data file suggests that Ben wants to use a Microsoft Exchange server rather than keep folders locally and use POP3 for e-mail, it vehemently refuses to do anything else, like start up far enough that it's possible to reconfigure it from within the program.
But fear not! The Microsoft developers thought of a convenient way to reconfigure this! All you have to do is switch the Control Panel back to Classic View (this isn't available in the hierarchial view that defaults on XP and XP Tablet Ed'n), open up "Mail", delete the erroneous Exchange Server account it automatically put up there, say "yes" to its repeated dire warnings, create a new Personal Outlook Folder File, give it a name and a storage area, encrypt it with a password (I didn't know you could do that in the first place), compress it, and then repeat the entire process to set up the first e-mail account. You must set up an e-mail account, even if it's deliberately bogus, before Outlook will switch its folder file over. How convenient.
Note that I rummaged through the built-in Outlook documentation for a great deal of time looking for the "how to set up a new Outlook data file because the current one is totally fucked" instructions, but they were not there. It required a search of the MSDN online knowledgebase before it even pointed me in the right direction- under a heading with some seemingly-unrelated title and completely different symptom that sounded suspiciously related to me and, apparently, was.
I am not thrilled with Microsoft's documentation or handling for this situation. There's got to be some less-obfuscated way. How about letting the program ACTUALLY FUCKING START with a bad data file and then bring up the full configurer? Not a one-shot dialog box to reconfigure the current fundamentally wrong settings ("Please enter the address of your Microsoft Exchange server" "I DON'T FUCKING HAVE ONE!" "I'm sorry Dave, that address could not be found"), but the full configurer. Preferably one that understands the concept of "Yes, my current settings are totally ruined" and doesn't give you three billion "THIS WILL OVERWRITE YOUR SETTINGS AND PREFERENCES AND BLALRGRGARGLALRGRGGHGHHH" warning messages every time you try to change a setting.
The problem is that it usually works right the first time. Ben set his initial settings wrong, and Outlook went bad from there. Very few people get to see this level of sheer suckitude in Outlook because they don't have to set settings twice. But still... that doesn't excuse error handling that bad, and that undocumented.
Also, 36 userpic spaces? I seriously need to figure out how to use those.