If your friend insists on "up-to-date", meaning a vast program that he'll never use more than a tiny fraction of, I advise you inform him of the "trial" versions of operating systems and office suites available on the torrent sites, and wish him luck. There's no profit for you in attempting to argue him into assessing real requirements and using the antique but entirely adequate solutions available with OS/2; at best, you'll only get blamed when he doesn't bother to learn how to use simple tools, because he's been programmed to think that "up-to-date" will magically imbue him with eloquence.
After a few days, here's what's happened: he's decided to stick with Windows for now, but I went ahead and installed my dusty copy of eCS 1.2MR. I had 4.52 installed, but it was being recalcitrant about a few things I wanted to do with it, so I found my key to eCS and loaded it up. So far so good. I'm running it on my small IBM NetVista (I've actually written an article on this website about that computer). Here's what I've installed for needed applications:
Web/email: Seamonkey 1.11
Instant messaging: SIM (don't know what version)
IRC: OpenChat/2 + gemZ (my favorite IRC client)
USENET: ProNews/2
Office Suite: Lotus SmartSuite
I've found all of these to be quite satisfactory for me, including LSS. It's got recent-enough formats for me to work with and if not, I do have a laptop with XP and OpenOffice installed on it in case of "emergencies". Overall, I'm quite happy with everything save for not being able to play Flash objects properly, but that's more of an annoyance than a genuine concern. For me, personally, newer is not always better. My current setup works great for me...as does my OS/2-based BBS server and my OS/2-based web server.
FWIW, he's not, as you put it, "...been programmed to think that 'up-to-date' will magically imbue him with eloquence". He simply wants to make sure he can do work from home with certain files. He's not arrogant like a lot of Linux and Windows users are; he just needs what he needs. Maybe some time with me and seeing how well things are with me will change his mind, who knows. I have taken ungodly amounts of crap from friends, co-workers and idiots on the Web about my choice in OSes. Then again, when theirs blows up in front of their face, I tend to say "told you so".
--Sean
P.S. Plus, I don't have precious resources sucked away by anti-virus or anti-spyware programs either. An additional bonus!