Ok here goes. Question proved more difficult than I thought. It's always tough to nail down five tobaccos. We truly live in the golden age of pipe tobacco!
Cig Smoker:
Haddo's Delight - yes, it's strong. But the nicotine shouldn't be a problem for the cigarette smoker. Really demonstrates what pipe tobacco is capable of delivering on all fronts: flavor, complexity, aroma, tin note, nicotine.
Angler's Dream - Inexpensive, satisfying for the burley smoker, absent the heavy chemicals and preservatives of OTCs.
Irish Oak - delivers the smooth, light VaPer + natural cavendish of LBF but without having to deal with the flake medallion. Just one less thing for the nicotine-addicted beginner to learn or fiddle with on the way to enjoying his or her tobacco.
Frog Morton - seems to be the universal English recommendation for new smokers.
Dunhill Royal Yacht - great demonstration of how straight Virginias can taste.
Non-cig Smoker:
LBF - inverse to my Irish Oak recommendation above, thought being that non-cig smokers may be initially more attracted to the pipe as a hobbiest and would enjoy fiddling with the medallion.
Erinmore Flake - unique topping, non-goopy.
Frog Morton - same as above
Dunhill EMP - light intro to VA/Oriental blend, good contrast with FM to determine Latakia preference.
OGS - Good VA intro, mild topping, inexpensive. Cool presentation in 100g tin.