"How do you learn the best and worse ways to play such holes? By playing many times, in varying conditions?"
Jim:
Yes, of course. That would seem to be the most effective way to learn how to read a golf hole and play it, don't you think?
"Any examples of this type of hole?"
There is. There's a particular hole at my course which I guess is fairly subtle, at least to a fair number of golfers, I suppose. The reason I say that is about eight years ago I wrote a design evolution report of my golf course in which I also wrote how I felt various golfers should play each hole.
And a number of members came up to me and explained that on one particular hole they realized, as a result of reading my report, that they had been playing the hole wrong for years, in some cases for decades.
I asked each of them how or why that was and was consistently told that they had hit what they felt were good shots which consistently came up wanting at the green end.
This particular hole had very little shot dictation off the tee.
I then asked each and every one if they'd ever considered trying to play the tee shot to the other side of the fairway (as I said in my report) instead of in a direct line to the hole?
Each of them said they never had.
I guess I could've asked them all why it was they failed for so long to learn from their strategic mistakes, and certainly as they felt they were hitting decent shots, but I felt that would perhaps be a bit rude or demeaning.