Hi,
I think what you are looking for is to have one video clip playing in the background at full screen size and then smaller windows playing on the screen, correct me if I'm wrong. This can be done in a video editing program like Premiere and I'm sure others with multiple audio and video tracks. You place the main video on track 1 and then your smaller versions on subsequent tracks but resize them to say half the width and height of the main video and position them in one of the four corners. You will need to use keyframes or an audio filter to fade the sound out of one clip as it is finishing and fade the sound of the new video up as it starts to play.
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