You can try the windows easy transfer if you're willing to give it a try.

http://support.microsoft.com/kb/928634

There's really no reason to remove windows mail. (There is no OE on vista, it's called Windows Mail.) You can make outlook his default email program. You should be able to install his MS Office on the new computer. I have office standard (upgrade) installed on several of my own computers, using the same license. The migration tool will tell you what you have to do.

Once you get his settings and data migrated, apps installed, etc, they you can decrapify it, by removing whatever programs you want to remove, and getting rid of task tray programs that start themselves, but don't have to, and turning off unnecessary services. I usually use black vipers web pages to research services and usually go with the "safe" option, for the most part.

You'll have to decide if you want to disable User Access Control or not. Once you disable it, I've found it's nearly impossible to re-enable it if you want everything you installed/updated after you turned it off to continue working. The safest thing to do is to leave UAC enabled.

I turn off all that sidebar stuff in vista (your dad's choice if he wants it or not, I guess), and I think Dell includes their own version of a mac-like application bar interface that you might want to keep or turn off also. It is pretty nice looking, but you really don't need it.

To research startup apps, I use this: http://www.sysinfo.org/startupinfo.html

BV's Vista SP1 services configuration: http://www.blackviper.com/WinVista/servicecfg.htm

It probably goes without saying, but the first thing you should do with the new computer is get it up on the network and do a windows update.

-David