I'm not advocating to use limited release bourbons, but when 90% of your drink is the base spirit, you'll get a lot of value out of using a traditional top shelf bourbon vs well like Jim. Try a $40 bottle like Eagle Rare or Angel's Envy. There's not much syrup in a good old fashioned -- go with 2oz bourbon, a teaspoon of simple or good maple syrup, and a couple dashes of Angostura. Maybe a dash of black walnut bitters, too. The higher quality whiskey should be apparent.