Haven't updated in a while, so figured I would give you the latest and greatest...
Oh man, I have to say the latest upgrade to Handbrake has helped me to replace all the software from before. Now I no longer run a Windows machine in my Virtual Box to be able to DVDShrink and then AutoGK the video into the format I want. I just use one tool, Handbrake.
They now have a Linux GUI as well as presets for "PS3" which is great in quality and has a relatively small file size, usually 1.8 gigs for a normal movie (90 mins). Because of these two things it has made it much easier, and you don't have to be a complete media geek to use it anymore. The PS3 loves it and plays it fine, so I think I have found the magic formula I was looking for, now I just have to figure a way to get the right command line so I can automated the thing, just drop a disk in and crunch away. If anyone has done this or has ideas would love to hear them.
Mediatomb is still doing great for me from a DLNA streaming server although it's really showing its age. I read some of the functionalities of the newer version of say ORB or TVersity, and Mediatomb cannot compare. But I read the next version they are working on for Mediatomb will have these functions and more, we will see when it comes out. It's still a little flaky in that sometimes it will make my PS3 say "Unsupported Data" or some other type of error, and I have to delete the Mediatomb database and recreate it and it seems to fix the issue.
I don't want to run ORB or TVersity on a Windows virtual box, they both require some good amounts of CPU since they transcode most things although I read that Orb has modified their code now to not transcode things that go to devices that support the media it's being sent. Okay rambling now, so I will close it off with I have found something else called Galleon for my Tivo's that looks really promising, I will post more about that next time.