OK, here we go with a fairly typical Newbies point of view. I am not a CS major, but I am a PC technician. I have been using DOS/Win for more years than I care to remember.
About 12 months ago, I started hearing more & more about Open Source software. To cut a long story short, I am now running exclusively on Open Source (FreeBSD) and having a pretty good time of it all up.
But the biggest let-down is with the lack of clear documentation with applications!
As has been said before, man pages have their place, and I browse them assiduously, but they are not the best environment for Mr Average User.
Installations aren't that big a problem (now!), though they were at the beginning. Setting up the programme to actually do what you installed it for seems to be the most neglected area, at least for me. Some of the options available are either just plain cryptic or downright geeky in their approach, "Enable Alpha bump-mapping? Y/N" I have no idea what Alpha bump-mapping is, though it's probably something I wouldn't want my daughter to consider doing!
Some (relatively) brief explanations of what each option allows/disallows would be nice. You don't need to go to the lengths that, say, The GIMP went to (a truly excellent manual), but at least something would be nice.
It is my aim to have some of the professional offices (Medical, Veterinary, Dental) in my area, start using Open Source OS's and software in their daily operations. Unfortunately, the lack of easy to access documentation makes it very hard for us to implement many of the appropriate applications, so Open Source misses out again, in favour of Redmond, who, if nothing else, has plenty of documented ways around the shortcomings of their offerings!