www.makemkv.com

Try http://jonthn.free.fr/MKVtoolnix/ linked from http://www.bunkus.org/videotools/mkvtoolnix/downloads.html#macosx I could test it when I get home, but it should come with the command-line programs. Since the only missing piece in your process under OSX seems to be getting the .sup, this should be ...

Here's what I've been doing lately (on windows). 1. (~30 minutes) Rip main movie using MakeMKV 2. (~10 minutes) Extract PGS streams from the mkv to .sup files using the mkvextract CLI program, included with the mkvtoolnix ( http://www.bunkus.org/videotools/mkvtoolnix/ ) package 3. (~15 minutes, depe...

I use handbrake myself. There's lots of threads on their forums about encoding profiles, but the default "high-profile" preset will probably work fine for you. I also use mkvmerge to mux in audio/subtitles after the video is compressed.

Do the mkv's contain blu-ray subtitles? I was getting crashes because of that.