I had a similar fascination with the stock trading component of the Railroad Tycoon games. I am almost ashamed of the number of times I tried to make myself a virtual fortune by destroying my own virtual railroad company.
It was almost always more effective to gobble up debt and then invest the money in productive capability if you were looking to earn a real fortune though.
The balancing act was to not overdo it - depressions was not fun if you were overly indebted.
Shorting the stcok of competitors were always good fun though, but mostly since they were so horribly bad at building which resulted in that it was sometimes a good idea to shorten stock.
Sigh - how I wish for a spiritual successor to Railroad Tycoon 3.
