Thank you for the info. I appreciate it.

No it won't.

but it wont randomly play XX minutes from a file randomly in random positions?

say it picks video #20 and chooses to play it starting at 20mins and then plays it for 8 mins or until end (8 should be configurable) then randomly select another video to do same?

You can use start and stop time to play a certain section of a file.

I would like to be able to play random parts of random vids for random amount of time (time configurable). Is this possible with mediamonkey?

Most players have random.
Most players have preview

Not much exists out there for randomly playing bits and pieces of videos or songs.