I do alot of video encoding to MKV/MP4. Retaining the original quality with a DVD rip is EASY. MKV uses a codec called "x264", which is what Blu-ray is using, only under a different name. I can post a few tutorials on here from another website, that show you how to rip a DVD, Setup the proper settings, and encode it. The process depends on how fast your computer is, for me it takes me 15 minutes or less without filters, with filters its 30 minutes.
If your interested, let me know.
About the MetaData, the only application that I know that works with that sorta deal is YAMMM, but it doesn't support TV-Shows up. I'm hoping to work with the creator of YAMMM to push out faster releases, but so far no dice D:.
To Rip a DVD:
I use the latest version of "DVD Decrypter"
Once you have it downloaded, run the installation, install it. So far, I haven't had any issues on Windows XP 32bit/64bit, Windows Vista 32bit/64bit, and Windows 7 32bit/64 version. Go into the settings, go to IFO Mode, change the Drop down box to "None". Save your changes. Now, go to "File Mode", select IFO Mode.
Now when you rip your DVD, it will rip it the way a DVD Player will read it. It will give you all the proper chapters, the exact episodes, etc.. It's a very handy program, if you need a video tutorial to figure out what to do next, lemme know.