Another board game I thought of that would make my top 5 list is called Acquire. I haven't played it in quite a few years, but want to add it to my stock of games. Here is a short description for those not familiar with it.
Description
As a powerful real estate tycoon, there are only seven hotel chains in the world worthy of your attention. Using nothing but your wealth and wits, you must vie against other business magnates to manipulate construction and capitalize on mergers -- buying, trading, and selling stocks in order to get the greatest return on your investments.
Acquire challenges you to pit your resources- resolve against other players in this high-finance game of speculation and strategy!