Just a thought here, but if you're heading to Louisville this winter you may want to visit some of the more bourbon-centric bars there and try a "flight" (sampler) of bourbons. These will usually give you about half an ounce each of three bourbons. Pick one with a known "good" whiskey and then see what it is you like about it and see if those flavors are present in the others. Some places will even help you design a flight to try some things side by side.
One thing you might like to try are Canadian whiskies. While sharing many of the underlying flavors of bourbon, they tend to be a bit lighter and less spicy and usually a bit lower in alcohol (this will result in less burn). These could even be considered as a entry level American whiskey. In this vein you might like to give a shot to Cnandian Club Sherry Cask, Canadian Club 12yo or the ever popular Crown Royal. These may give you a good base to work off of while you grow accustomed to the more intense flavors of the higher strength/older bourbons. Canadians also tend to be extremely well balanced and drinkable. While some may consider that "uninteresting" I think it is a quite enjoyable experience, consider it like chillin' with some old Beach Boys as opposed to thrashing with Metallica.