Hmm, this would be a difficult hack to make, unless you enable HTML in your signatures I suppose.
Here is my suggestion:
Create X amount of new fields (lets say 4) in the usercp profile page under the signature field. Then allow the user to enter up to 4 different URL's of signatures. Then you could probably work your way somehow with one of those banner rotation scripts and integrate it with vBulletin to allow a member to rotate their 4 banners. You could have more than 4 ofcourse, or you could even allow the user to specify how many he wants, ofcourse this adds more coding on your part.
Attached is the simplest banner-rotation script I know of.
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