If you choose Xandros, you can use Cross-Over Office to keep certain Windows aps on Linux. Or if you have Windows 98 you can run it on top of Linux with Netraverse's Win4Lin so you get the best of both worlds. Your choice.
IMO, Linux would do very well to set up local user/advocacy clubs to offer a leg up to newcomers. I'm at the point where my initiative to take on a huge shift in computing habits is near nil. I need to see the OS modeled IRL. I suspect there are many who for various reasons would be in about the same boat. The demand has to be ratcheted up in order the whole thing to reach critical mass.
I have copy of Xandros, haven't installed it on anything as yet...hoping it has better multimedia support than Fedora Core 2.....