Couldnt find any examples of that in either NFL:
http://www.profootballhof.com/history/release.aspx?release_id=1286
or MLB:
http://www.baseball-reference.com/bullpen/Expansion_of_1993
http://en.wikipedia.org/wiki/1998_Major_League_Baseball_expansion
Seems all teams that came in at same time, paid the same fee.
Problem with your scenario, which I realize was extreme to prove the point, is exactly that. Rarely is their that huge of a disparity between buying the gold mine or the barren land. Most of the areas usually lie somewhere in the middle, and whether you find a goldmine or waste away has almost as much to do with the organization itself (how it's run, etc.) as opposed to where it's actually located.
I don't think Hamilton is the proverbial "gold mine" either. You've got fierce competition from two long-standing franchises in Toronto and Buffalo on either side of you. Not to mention your costs of doing business are going to be a lot higher in an area like that then you'd have in say Winnipeg, where you have the added bonus of not having to build a new arena and you're the only game in town.