What do you typically like to drink? Higher alcohol will take a bit to get used to regardless, but there's a reason the basic bitch brands sell the most. They're typically the most friendly. Having a lower alcohol content (40%), filtering, sweeter flavors, blended barrels, etc. typically make for a more friendly product, but after the taste is acquired people typically gravitate towards something more expensive. Chasing/mixing it with a drink you all ready like is a great start because it will lower the abv even more and help acclimate you to the taste.
A charcoal mellowed {Tenessee} whiskey such as Jack Daniels or Dickel, or better yet a double filtered one such as Gentleman Jack,or a sweet canadian whiskey such as Crown Royal are great ways to start. Irish whisky's such as redbreast 12 or a fine Japanese blend such as Hibiki Harmony are almost universally enjoyed.
Some prefer the profile of whiskeys aged longer in a barrel. Even though you don't like the 6-8 year buffalo trace, you might really love the 8-12 year Eagle Rare of the same mashbill and distillery.
Since taste is subjective; there's really no telling what you might enjoy best. I'd suggest finding the mini 50ml bottles of every genre, or at least the most extreme differences, and honing in on what you enjoy most. You could also try a local bar that offers "flights," a set of mini shots of various whiskeys. Even though most beginners don't enjoy more complex and harsh whiskeys, it would be worth trying some barrel proof/cask strength, smokey Isla, and typically bitter/spicy rye whiskeys.
While not actually whiskeys, you might also want to try flavored liquers with whiskey such as Fireball, and any of the various brands of bourbon cremes, honey/peach/cinnamon/apple/vanilla flavors from Crown Royal, Jack Daniels, Evan Williams, etc.
