Welcome to the forums
A good way to taste a lot of different bottlings, would be to locate an wellstocked bar, where you can try by the glass, rather than the relatively expensive by the bottle option.
You could also find some likeminded souls and start swapping samples or buying bottles together.
I take it that you are mostly into bourbon / American whiskey? If so, you should really visit http://www.straightbourbon.com
, where you'll find a dedicated bourbon forum.