I would try linux again if they applications were there but they just arent. You can browse, IM etc... but I do more than that.
I felt this way until a year or so ago when i switched to Ubuntu and started using linux full-time. Turns out I've been able to find an app for almost everything I do, in the standard repositories, no less. The sole application I use that doesn't run on linux runs just fine under Wine. In my experience, Linux is there.
Gah, are we gonna do this again?
Since 99% of home users don't understand what is going on, all it would mean is more computers would be going to the shop for simple cleanings.
You say that like it is the users fault, however, poor documentation and complex UI design (although completely off topic) is equally, if not more at fault
Port this analogy over to automobiles, rather than planes(a bit more appropriate, since you actually operate an automobile/PC, unlike a plane) and it actually supports the parent's statement. Unless it's something that I understand and can fix(out of gas, flat tire..etc), when my car doesn't work I take it to the shop.
How about starting with good, old-fashioned requirements gathering?
Talk to a few people for as many roles as you can determine. Find out what features your office currently uses, and prioritize and categorize them(must-haves, costly-to-lose, frivolous[quantified as much as possible]). Compare this to the equivalent(or NONequivalent OO features). This data will tell you exactly what to do.
Classic cost-benefit, imho. Use leg-work and good analysis to make the right recommendation, not buzzwords and advertising.
Once you make the right decision, selling it to the masses is easier than you think. It's those decisions that are made with no real research or for the wrong reasons that aren't accepted and blow up in your face.