please search "DVDshrink" first
if you don't wanna pay, there is nothing like DVDshrink for Mac.
You can consider mac the ripper, handbrake, isquint, dvd remaster etc, none of them is as good as DVDshrink, but can do the job some way or another.
yes you can do DVD shrink in windows. But remember DVD ripping is a CPU intense work.