After looking over these lists, I think we need to first agree what is a penal hole. To my mind, a penal hole is one that offers no alternatives, no options, and demands that a shot be played a certain way, or to a certain area – no exceptions without penalty. A strategic hole, on the other hand does offer alternative routes and strategies, that rewards the bold or heroic shot.
Of the holes listed that I have played, I would have to say that in my opinion neither #16 at Cypress, nor #8 at Pebble qualify as penal holes. Both holes offer options to the forced carry approach. As MacKenzie himself has pointed out, #16 has been played in match play, and WON with only a putter.
I have seen #8 at Pebble referred to as penal in another thread also, again because of what is perceived to be a forced carry. I disagree; it is not only NOT penal, it is the essence of strategic design. The hole can be played completely over land, if one so chooses -- drive left, layup left, and approach to green over cavernous left bunker. So in my definition neither of these holes qualify as a penal.
#15 at Cypress however has no alternative route, and I think this would qualify as a penal hole that is fun to play.
To get back to Patrick’s original question as to why it is both fun and penal. I think the main quality that raises a penal hole to the level of fun is that one of the shots must be thrilling, and there must be no alternative to that shot, no strategic options. There must be an element of terror or fear of failure that is outweighed in reality by the ability of the golfer to physically perform. MacKenzie said many times that he liked to create holes that were visually much more intimidating than they were in fact. This provides the golfer with a tremendous sense of accomplishment, of having stared into the face of fear and not blinked. A short carry like the one at #15 is a feat that most of us are capable of pulling off. But it can still be scary and thrilling as hell.
So to summarize, I think what allows a hole to be both penal and fun is
1) a sense of fear and intimidation to a shot, that is more psychological than physical; where there is no alternative to playing that shot,
2) the thrill of accomplishment that comes from the successful shot
3) in the case of forced carries, one that is short enough to allow us a real physical chance of accomplishing it.
I think #17 at TPC is a hole that walks a very fine line between being fun and being drudgingly penal. Given the possibility of Florida winds, and no real bail out area, there must be times when the hole is just hell to play. I don’t think I would want to play a hole like this at any length LONGER than what exists now. I think it is right on the border. However, for these very same reasons, it is a great hole for professional tournament play.
A thought that just occurred to me while writing this is, perhaps this is what makes a great strategic hole – one that walks a very fine line between being penal and strategic. One that provides a thrilling sense of accomplishment, terrorizes us, and goads us into attempting the heroic shot, even when an alternative route exists. Just a thought.