Kinda-sorta. When I upgraded from XP to 7 on my desktop I stuck Burnout Paradise and Crysis 2 on my external drive, along with all the stuff I wanted on steam. When I went to reinstall everything, Origin detected my Crysis 2 files and just slapped what it needed to into my registry. If I want to play Burnout Paradise, though, I'm gonna have to redownload.
Steam sales. There are at least 9 every week, including mid week madness and weekend deals.