Gnash doesn't work well for anything, and in fact gets in the way of fallback
HTML5 players (making some streaming sites look like they don't work when
they do). I have no idea if Wine works with Skype, but it's probably not a
high priority what with a GNU binary being available.
Sure, you could give your friend Trisquel with Skype added on, but what would
be the point in that? They're going to get no support for that from this
community, and they might decide that Trisquel (or worse, "Linux" or
"GNU/Linux") is stupid. If they're unwilling to stop using proprietary
software, you might as well give them an imperfect system whose community is
going to help them. Take it one step at a time.
If they already know about free software and understand that proprietary
software is bad, that's a different story, but most people who are used to
Windows don't even know about this issue, much less understand it.
