you'd be surprised how many progs will "just" copy.
generally speaking ... the bigger the less likely (office!)
progs for specific devices won't copy
but the best way to settle the argument is to do it ... just be aware that it might not.
progs with a serial no will almost certainly need re-registering and if you have the cd or install file ... don't mess about - just reinstall
finally do be aware that a usb stick is about as unreliable as it gets.
the design is full of bad possibilities
it's also very slow ... yes you can get 4Gb from tesco for �8.98 - but filling such a devive with small files is a n overnight job
use
http://www.download.com/TeraCopy/3000-2248_4-1 0671835.html
they are cheap - so are built to a very low budget
they stick out of a hole in your PC so are easy to snap or damage
the type of memory used will reset over a few years - a cd won't
and finally ... they are easy to loose (I've lost 100s - but I did find a lost top under the bed .... how it got there I don't know)