Okay, my second round of cigar/bourbon was enjoyed this afternoon. Today I tried aforementioned cigar with Pappy Van Winkle 15YO 107. Both were enjoyable but not as good as the last combination of Davidoff Millennium with Evan Williams Single Barrel 1995. I finished the PVW before the cigar so I tried the EW SB to do a little taste test. I liked the EW SB a little better as it seemed to go better with the cigar.
Sorry I cannot provide better information but unfortunately my pallet is basically "I like" or "Don't like".
Any other combination suggestions or comments are welcome.