My brother quit Linux Mint despite having huge slowdown problems with Windows
probably because of a combination of a few small issues (some driver issue
with the video that caused bad 3D graphics, trouble with his wireless, and
lack of nonfree game support). His conclusion in the end was that "Linux"
sucks. (For the record, his laptop has Intel graphics, so I doubt it was a
bad hardware issue; he probably just needed a kernel update.)
The thing is, some people are going to be impatient with new things, so if
just a couple things go wrong, they will decide they want what they are used
to back.
I think completely replacing a working Windows system that someone is used to
with a half-working GNU/Linux system that they are not used to is an unwise
idea. If Trisquel can work without missing any important features (in
particular, WiFi on laptops), then introducing it to that person is a good
idea, but it should be installed alongside Windows, not in place of it.
Dual-booting allows the person to transition as his/her own pace and retreat
back to the familiar system if a seemingly terrifying problem arises.
If Trisquel can't work without missing important features, I think it's
better to introduce free programs that can run on top of the system they are
using, such as LibreOffice, Firefox, and GIMP. Then, the next time they are
out to buy a new computer, help them pick one out that will work well with a
free system like Trisquel, i.e. Intel graphics, HP printer, a wireless card
that works, and a sound card that works. Then install GNU/Linux alongside
Windows so they can get used to it.