Authoring a DVD is based on programming code - I do not know of any randomize generator that was built as structure for the code. Hence what you are supposed to do with a DVD is program very specifically what you want to occur.
Interestingly you can get random (read that unpredictable) effects by creating a 'sloppy' coded DVD that will respond differently based on the set-top player and its corresponding firmware.
So I think you should best explain what you want to happen and then see how it can be programmed - then that will happen player to player for the viewer.
I am creating an educational DVD that asks questions at the end of the video lesson.
In order to get the video to be a littlie different each time its watched, or for each student. I was trying to come up with about 9 total questions but only ask 3 at the end of the lesson. If the 3 that are asked are randomly picked from the 9 then the student watching the DVD could have a somewhat different experience each time through.
I know you can randomize items in a playlist but the playlist doesn't give you the option to use menus. And a menu is where I have the questions with each different answer (link) going to another video or menu.
What you are attempting on a DVD was once the province of products like Media Toolbook, and more recently html and xml coding for the internet experience.
I don't think that what you anticipate the user experience to be with the process you have outlined is all that worthwhile. Companies undertake this kind of education delivery with a lot of field testing to verify whether the user experience justifies the means to get there. I just don't think it would be worthwhile.
On the other hand you can create interesting DVD's with presentations 'peppered" with pick an answer to a question - and then based on the pick - you redirect the viewer to another presentation. This can be done (not easily) with a limited ( 3 or less choices per a few questions) over the entire DVD volume.
Doing so can be done by employing menu pages (elements of menus) and/or DVD scripting language. When you think you've authored your masterpiece, test, test, test.
Thank you for your input and suggestions. In my quest to make an exciting educational DVD I guess I didn't take time to think that studies have already been done on this sort of thing. I guess your saying its an overrated experience for an educational adventure.