I think onpon4 sums it up pretty well.
Free software in general, such as GIMP, is a step in the right direction. A
GNU/Linux distribution such as Ubuntu or Fedora is an even bigger step in the
right direction-- even if both have proprietary software and firmware.
I wouldn't recommend Trisquel to someone who isn't interested in or doesn't
understand free software, quite personally. Especially if they are accustomed
to a proprietary operating system where everything "just works" out of the
box. I don't think your friend will appreciate having to use a special USB
wifi card, or degraded 3d performance, or not being able to use programs such
as Steam, After Effects, what have you.
I think most people (and your friend) will just come to the conclusion that
their old proprietary operating system is better because "it just works",
despite the upsides of free software. They won't have to go through a bunch
of trouble (such as buying new hardware) to make their once working computer
function properly again (if the hardware is incompatable with free software,
of course, which in my case is rather frequent).
I had a lot of trouble making the decision to choose free software. It took
me a while to choose because I saw practical (at the time) gains when using
some proprietary software and firmware. I didn't want my hardware not to
work, either. I didn't want to replace something that once worked. But, I
eventually got fed up with proprietary software all together for security,
privacy, ethical and liberty reasons. Not to mention the costs of some
proprietary software.
If you give your friend some time, they may choose the path of free software,
like myself. But, I believe only if they understand the reasons for choosing
it and are willing to go through some extra difficulty for good.