Josh - Our process is very similar. Mine goes like this...
In a beaker (stored in the freezer) I toss in a sugar cube, a Jack Rudy cherry and two dashes of bitters. Muddle.
Once muddled, I throw in two large blocks of ice and a jigger or two of your favorite Rye, Bourbon or Whiskey. Stir.
I stir for about 60 seconds. But time can be adjusted to your liking. Shorter if you like it stiff.
Pour into a heavy bottom old fashioned glass (also stored in the freezer) while straining. Add large ice cube before straining if desired.
Finish with a nice zest from the orange. Run orange peel around the rim and enjoy.
IMO, the zest is the key. Smelling that orange while sipping the drink is what dreams should be made of. I put it up with that 68F, sunny afternoon, smooth asphalt, no traffic, 6 mile descent.
Take a look to see if Clyde Mays is available to ya:
Clyde May's Whiskey
Jack Rudy cherries. Devine!
Bourbon Cocktail Cherries - Jack Rudy Cocktail Co.