That's called rotoscoping - very work intensive and it needs specialized software, although there are rumors that Vegas may have suitable plug-in's coming.
Do a search on Rotoscoping and find out all about it.
I did something like this once. I had to export all the frames to png's, then go into photoshop and edit each picture individualy. Took about 2 hours for a 5 second clip (was a big area, little detail).
I should mention, though, that i got the look I wanted and it was worth it.
Hmm, I'm not sure if I understood the problem completely... but principially you can make a mask for a moving object as well, as long as the background differs enough from the object. You can apply a "Chroma Key" filter and pick the background color (there are already presets for blue screens), and use its "Show mask only" checkbox. Probably you need to play a bit with thresholds and maybe add contrast&brightness. After rendering, such a clip could then be used as mask for your original clip.
Yeah...I guess what I was looking for was doing vector paths around objects like in Boris Red....which I can't afford! :-0
Other than that...I guess doing frame-x-frame paint out is the next best. Time consuming, but it probably is the best method for a shot after the fact.