Visually the randomization could be done easily, but there would probably be no "transitions"; you just hard cut or fade to black between each segment. Musically, it would be a bit more challenging. Each segment would have to be composed as a mini stand-alone musical idea; they would all have to be in the same key and cadence at the end. It would be like composing a theme and set of variations; a "fixed" opening would establish the theme, the middle portion would be the random assemblage of "variations", and it would end with a fixed coda to bring the piece to its finale. The overall effect, however, would be like beads on a string vice a sweeping panorama. An interesting "trick" would be to have each segment end on the dominant or subdominant of the key, and then start each section on the tonic of to complete the cadence. This would Aurally cause each segment to naturally lead into the next. But of course this would have to be completely mapped out before the project was ever started...