Advice for a specific shot.

Ok so in this film I’m planning I want to open with a hand held shot following closeup behind the two actors as they walk along this bridge and then as they get to this alcove they look out and the LA skyline is revealed and it’s half destroyed and that’s where I want to put a matte painting.

Is this something do able? How hard do you figure the roto and motion tracking would be for a shot like this? Also how would I go about doing this. I have sort of limited experience with roto and motion tracking but I figured I could freeze on the last frame I want turn that into a matte painting then track the image backwards to the first part where you can see the skyline and roto around the actors. Would that work?

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