I've used Linux for years and I would never suggest it to anyone unless I was confident they were pretty computer savvy. Otherwise as the suggester you are on the hook for getting all their windows programs to emulate in WINE or to find alternatives or to track down their missing dependencies.
If you look at my original suggestion, you'll see I specifically suggested to use Ubuntu if they don't need the Windows compatibility. True, Wine is a PITA, but even when I started using Ubuntu as a dual boot, for fear of not being able to run Windows programs, I soon discovered I didn't need them at all. And, for the ONLY Windows program I need (Solidworks) I have a second PC, just because my laptop hard drive is not big enough to dual boot Windows 7 and Ubuntu.
About your second post, I can put myself as an example: I'm definitely NOT as clever as you may think, yet, if you go to the Ubuntu forum, you will see, in the year and a half I've been a member, I only started 16 threads, and several of them had nothing to do with Ubuntu itself.
The fact that you have to read up and learn how to install programs instead of just clicking an executable and clicking NEXT NEXT NEXT, (which can be a feat in itself for some) means the average PC user isn;t going to want to deal with it.
Now you really lost me. What version of Ubuntu do you have?
I'm asking you this because I started with 9.10, and now have 10.04. I have installed many programs in both, and never had to do anything other than to look for the program in the software center, and click "Install", period. Very few times I have had any problems with them at all, and, when I did, it generally took me less than 5 minutes to read up the forum, and fit it.
I am pretty computer savvy. Ran Linux a few years ago. It was workable, but just kind of a pain in the butt. Went back to windows. Maybe someday I'll try agian.
I'm really not computer savvy at all, when it comes to software (with the exception of viruses, that have been my obsession for almost 2 decades). Try Ubuntu 10.04. I have compared it to Windows (7. to the previous Windows versions there's just no comparison at all), and had other people compare them too. Everybody loves it.