There's a hole at the old Lake course at Deerhurst Highlands north of Toronto - the 4th, I think - that I've had a lot of trouble playing well.
It's a very short hole, less than 100 yards, perched on a high point of the property. The tee shot is played over a depression and slightly uphill to a shallow green guarded at front by deep bunkers and featuring O.B. over the back.
It's always been windy up there, too, which makes it key to strike the ball properly in order to pierce the wind and hold the green. [Personally, I frequently find it difficult to make a good solid strike from 100 yards using a sand wedge.]
Such a hole, in my opinion, can be a stern test under the right circumstances [particularly when it's windy, of course]. But, we rarely find 99 yard holes at "regulation" courses these days. Aside from the seventh at Pebble Beach, and the good ol' "2 or 20" hole at Engineers, where are some really good 95-110 yard holes found?
Rod Whitman has one laid out at Sagebrush (in planning) in British Columbia. And, Rod and I just inspected another site last week where I think the possibility for such a hole exists.