Sherry finished and lower ABV (no cask strength) tend to be good predictors for pairing scotch and cigars in my experience. I also avoid older whiskies, especially bourbons, as the cigar can bring out more dry wood and oak than you generally want to be focusing on in those older drams. Generally speaking, I’ve had more success pairing rum, cognac, armagnac, and port with cigars. They seem to do a better job emphasizing the sweeter and fruitier notes in cigars for me which tend to be more subtle than leather, wood, etc.