I am speaking from my "Vista without TV Pack" experience.
A ripped DVD (vob files) will only show up in the DVD Library (assuming you point the DVD Library at the containing folder), and that structure is the only one that you can use for emulating the functions of the actual DVD (menu, special features, etc). Without any alterations, they will not play on an extender, and I don't think there is any current method for the menu and special features to work on an extender.
If you convert from VOB to some other format, you will not get the DVD functions, only the video/audio playback. With some formats, you may lose seek/ff/rw.
If you convert your TV series DVDs to .dvr-ms files, you can use EditDvrmsMetadata to modify the title, subtitle and WM/MediaIsMovie tags to make them play as a TV series. You can put them in the Public Videos folder (or a link) and they will show up in the Videos strip. They will also show up in the Recorded TV strip just like a series recorded from TV.