One argument for including WINE is that it allows the use of hardware people
already own and need to use (eg pedometers, digital audio recorders and
cameras, cell phones), but that only works with the Windows drivers supplied.
When I help someone transition from Windows to GNU/Linux, it usually involves
the following steps:
1) dual-boot GNU/Linux (usually Mint to ensure the first impressions are of a
reliable OS that supports as much of their hardware as humanly possible) and
encourage them to try it out
2) help them troubleshoot any of their everyday computing tasks that don't
seem to work on GNU/Linux (this often involves installing WINE)
3) once, they are using GNU/Linux at least half of the time, encourage them
to delete their Windows partition, and use any devices/ programs they're not
ready to give up using WINE (which also gets them tinkering, increasing their
confidence in administrating their own GNU/Linux system)
4) encourage them to replace any hardware that depends on WINE (and/or
non-free drivers/ firmware) as they can afford it
5) once they no longer need any non-free drivers for their base system, move
them from Mint to a free distro, usually Trisquel
6) once they no longer need any non-free drivers at all, encourage them to
uninstall WINE
WINE is an essential part of the hand-holding involved in successfully
getting people from Windows to 100% libre GNU/Linux, without frustrating
them, and losing them along the way.