The approach into #2, especially when the pin is far right. I love the approach on #18 as well, especially when the pin is in that evil front-right corner.
I think that Pinehurst #2 may be the most misunderstood great golf course this side of St. Andrews (even after over a dozen rounds there, I still have a tough time figuring it out!). Every hole is full of options, but the problem is that the majority of golfers are not able to use them all. For example, on the 2nd hole, the contours on and around the green may be attacked in a number of ways; it is up to the player to decide what type of shot is best and then execute it. If the pin is center-right near the back drop-off, where do you land the ball? and at what height? and with how much spin? and how much curve--fade, draw or straight? I'm still trying to figure this out! There are a number of combinations that the player can try if he has the ability to do so.
How about the 1st hole: play down the right to open up the green or play left for a shorter shot but a tougher angle. But how do you play the shot from the left side of the fairway to the back/left pin? Do you hit a high spinning shot, a low-running hook, a standard shot to short-right of the pin, a bailout to the short or right chipping area that takes the deadly left bunker out of play completely?
So the strategy isn't always as simple as: hug the trouble & get the better approach vs. play safe & have a more difficult approach. The strategic options lie just as much in the shotmaking as they do with angles, placement of hazards, etc...
...in my opinion!