@leasematthew
A few more thoughts about Bourbon ...
1) if you really want to learn and taste, consider visiting Kentucky and spending a few days touring the Bourbon Trail. I was passing through Louisville last summer and went to Peerless. They are a very small producer, but also one of the oldest. Their Bourbon (and Rye) are amazing. Bit pricey but totally worth it. Old Forester is also in Louisville and would've been my second choice had I had more time to spend. I knew that I liked OF; but I now know that Peerless is a solid choice, too
2) If you're ever in Waco TX, visit Balcones distillery. Their Blue Corn Cask Strength Bourbon is to die for. Several other TX distilleries worth visiting; that state has some really good whiskeys
3) As you probably know, Bourbon (by law) must be at least 51% corn (in the mashbill) and aged in new American oak barrels. It can come from any US state. (Jack Daniel's is technically a Tennessee bourbon) The characteristic flavors that contribute to the bourbon's taste are found mostly in the other grains that make up the mash. Bourbon that contains a lot of wheat in its mashbill tends to be sweeter in flavor; EH Taylor is in that category, as is Weller's.
Bourbon that contains a lot of rye in its mashbill tends to be a bit more spicy in flavor (think Knob Creek, e.g.). The more you know about what's inside the recipe will help you understand and decide whether you like one of the grains (wheat or rye) better than the other; or enjoy them equally