Man, you are asking for a lot of vignetting and tracking - a time consuming task.
To be honest, I think the best way to attack this is to use Mocha to roto and track in AE. Then use the Color Finesse plug in for the color correction inside and outside the roto.
Pre-visulaization was key for Pleasantville. If you guys couldn't do that because of budget constrains or lack of resources your post production time is going to insanely increase to achieve the effect - if what you are looking for is perfection.
Either way, you are looking a lots of time.
Good Luck!
Stuart Ferreyra
Timecode Multimedia
Colorist / Online Editor
Ph: 310.826.9199
AIM: stuart.colorist
http://www.timecodemultimedia.com
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