Here are my deep thoughts on expensive bourbons:
1. If you like it, buy it but attempt to try it first to avoid dissappointment after forking over that C-note.
2. I have never tasted a bourbon worth $90 more than my AAA10yo or my Weller 12yo.
3. In a blind tasting, could you pick out the $100 bourbon over the $40 bourbon? I find that there are significant diminishing returns once you hit the $30-$40 range. After that the higher prices usually are a result of limited availability and not necessarily better bourbon.
4. If there was only one bottle of Elijah Craig 12yo in the world, and you wanted it for your collection, would it then be worth $100 for the same whiskey that now sells for $15?
5. I have paid $90 for a bottle of bourbon and enjoyed it very much!