Buffalo Trace, Eagle Rare 10 yr Single Barrel, any Van Winkle but that would exceed the $50 unless you can get them to bring you an Old Rip 10/90 or a 10/107. Maybe Old Grand Dad 114, Weller Special Reserve, Old Weller Antique and maybe a bottle of Sazerac Rye. That would be were I would start if I had to get stuff that is available anywhere. Oh and a bottle of Elijah Craig 12 year old as well. If you get into higher proof try Wild Turkey Rare Breed and always go back to the big WT 101.
Hope that helps