I picked up my first pipe this month, and I have to say pipe tobacco seems to have more versatility than cigars at both ends of the spectrum: it even pairs up well strongly-flavored teas.
At any rate, I'm not particularly adept at keeping the bowl lit all the way through yet (I've only smoked a few bowls), but I know I'll develop better rhythm as time goes on.
Based on my limited exposure so far, I'd have to say the straight Virginias or Virginia/Burley blends I've had seem suited to bourbon; English (i.e., including Latakia) less so. Interesting idea on pairing Latakia w/an Islay malt. Looks like I need some more Bowmore.
I'd like to keep discussion going on successful pairings, especially particular bourbons that do or don't work well.