Pat, interesting thread.
To me a course that is more fun (or appropriate) for match play is charaterised by an over-abundance of holes that are potential stroke-play round wreckers, where the threat of taking penalty strokes for a lost ball, OB, or water is constant. The poster child in my mind is course like Tralee, in Ireland. There are bottomless pits, tall grass, water and areas that afford no bailout or retreat. The Florida version: Old Marsh. There is water on how many holes there?
As you suggest, Fenway has OB left on the 2nd, 3rd, 5th, 10th, 14th and 18th holes. None on the right! (Not exactly a hooker's paradise.) There is also OB behind the 1st green as well as the par-3 11th. The player also faces OB-right on the 2nd shot into 18 (parking lot).
Pinehurst 2 iis often referred to as the most difficult course where the player will almost certainly finish the round with the ball he or she started with. Give me a course without OB or water for stroke play.