I understand the official stance on this topic...Any discussion of that nature could lead to the thread getting locked so lets all follow the forum policy on this
I don't think you do, we've never had a single thread locked in the 7 years we've been very openly talking about backing up dvds and blu-rays that we own. Apps like MacTheRipper, MakeMKV, Handbrake, RipIt, software players and front ends that play back ripped dvds, all openly discussed in hundreds, if not thousands of threads, here at AVS. This is an HTPC forum, how do you think those HTPCs are used...to only play back individual commercial optical discs????
Does anyone have any 'workflows' that work well to the point where I could leave things running overnight and have my systems just churn thru X number of native DVDs that I have copied to the HD?
Does anyone have such an automated system or something close to it?
No, here's where I think you're gonna be a little disappointed, it's naive to think it can be automated to that extent. It's worth your time to do it once and do it right, here's why: each dvd is different, differently encoded, different quality, different content type a la TV versus film, some have extras and menu structures you want to keep intact, others you just want the main feature, some have subtitles you need, on others you want commentary tracks, some you don't, many discs have really annoying structures or aspects you'll want to eliminate before transcoding, etc. So, my recommendation, even if automated ripping processes are available, discard them, rip a whole bunch of your dvds, one at a time, while you're sitting at a computer in your house doing something else, then queue them all up and let handbrake do its thing overnight. 600 dvds may seem like a lot but you're late to the party, so that's on you--you should have already been ripping and transcoding for years now.
Personally, I wouldn't do iso if you do Mac, go VIDEO_TS folders instead, easier to deal with in an OS X HTPC environment. And if the menu structure and/or extras on a dvd aren't that important to you, skip both altogether, rip right to .mkv with one of those commonly available tools (MakeMKV) and then let Handbrake transcode those .mkvs to whatever iPad or aTV2 preset you prefer.
There are too many variables with dvd and blu-ray to think you can come up with as painless a ripping/transcoding/importing system as for a music cd. Video remains much more complicated.