When I rip a movie to my HTPC I use AutoGK. It's easy and fairly quick. There are better alternatives out there that offer more options but I don't think I need them.
Easiest way to get a nice picture (sorry no description) is to create a folder. Name it the title of the movie. Name your video file the same name as the folder. Find a picture of the DVD folder (it has to be a jpg as far as I know) and name it folder. Drop that picture into the folder and now you have a thumbnail of what is in the folder.
Example:

As far as a manager I use SageTV. It does give descriptions of files but they have to be MPG or MPEG files to have it. Then again this PC was built to record TV and watch movies on (DVD player, file player, etc...).