I've been experimenting with this since this post started. I had never had an old fashioned (so thank you again!) and really liked the potential when I first tried it. But after a month, here is my perfect recipe:
.5 oz simple syrup (i had on hand and also im just too lazy to muddle anything, lol)
3 dashes Angostura
4 oz Bulleit bourbon
1 orange slice rubbed around rim and dropped in glass
1 cherry + 1 spoonful of cherry juice
4 cubes of ice
Thats my version of a "less sweet" old fashioned, lol.