Here's what I'd do:
1. Shoot a time lapse of the sky with clouds moving toward you. Be sure the horizon is low enough to be hidden by your cityscape graphics. This goes on track 1.
2. Shoot the road on a dolly. A wheelchair works as does a wagon with smoother pneumatic tires low on air. This goes on track 2 but be warned that you may have to move, enlarge or rotate it. You also have to crop the top of that video frame off so that it does not obstruct the sky footage. There is a New Blue effect that does this. I forget the name but it ends in, "...by shape."
3. Get a picture of your cityscape. In a paint program, make the transparent areas where the sky and road show through. This goes on track 3. Enlarge and position if necessary.
4. Now get a shot of you and your couch against a green screen (if you want it to be looped video) or just get a still shot and in a paint program put green all around you and the couch. Put this on track 4 and use chroma key. Reposition as necessary.
Now to loop the videos? To loop the road and the sky, go to the middle of each clip and split each one. Now swap the halves so that the second one comes first on the timeline. Finally, drag one into the other to create about a 1 second cross dissolve. Because the beginning and end of each swapped up clip used to be together, the loop will work.
Now make sure all tracks are the same length, produce the project to a video file, and use any method you like to play back a loop (like a tool that creates animated .gif files from video).
If you use video of yourselof against a green screen (waving or whatever, you can loop it the same way as the road and sky.
Len
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