Sorry - we can't help you break copyright law....
But ya, DVDShrink + Handbrake = Super simple and reliable method. Solution runs well on XP, Vista and Windows 7 (my own experience).
You should be able to comfortably complete ~2 discs per hour if you're not grabbing all the special content, languages, etc. My guess, 500 discs will take you 6-8 weeks to get done, allowing for 'life' to happen.