Is converting the least tech literate an issue? I assume some of the easier distros are pretty much plug and play now, and if your only goal is to browse Facebook and print off recipes from an already set up printer pretty much anything can do that easily. But these people would probably be happy with an iPad if their iPhone wasn't cutting it.
I think the big middle of the population that's the problem, people who are tech literate enough to do some things, but not willing to relearn the wheel. They can use microsoft office, but don't want to have to relearn a new file structure. Those are the people who probably will have the biggest issue, and there's a lot of them. That's office workers, computer gamers, all those people. Even the pretty tech literate people who know how to do things in Windows but don't care to relearn it all in Linux.
I think the big middle of the population that's the problem, people who are tech literate enough to do some things, but not willing to relearn the wheel. They can use microsoft office, but don't want to have to relearn a new file structure. Those are the people who probably will have the biggest issue, and there's a lot of them. That's office workers, computer gamers, all those people. Even the pretty tech literate people who know how to do things in Windows but don't care to relearn it all in Linux.