George,
I think you might have already answered your own question, IMO, combined with Phil's answer.
I really think most tee shots, straightword, with options, risky or wide open are really only dependant on two things:
1) From your own mouth, the level of skill you have as a golfer.
Obviously, the BEST tee shots would be on a course that does the BEST job of implementing tees that accomodate golfers of all skills AND assumes that the golfers themselves play the right tees. If every skill of golfer played from the tips, for example, I think the only interesting options and strategies would present themselves to the low handicapper. Everyone else would have a "straightforward", I'm-just-trying-to-hit-the-fairway mentality about the shot. Likewise, if everyone played the forward tees, the low handicappers would likely bomb their shot over all the intended hazards and not have to think twice, while the higher handicapper dealt with options and strategies.
2) From Phil's idea, the way you yourself feel about your game on that particular day, and how much you want to challange the holes.
Even on a hole that may only present a straight-away fairway with no bunkering, I might reach in my bag for only a 3-wood if I've been shanking my driver all day. Conversely, if I've been striping them all day, I'd probably be more tempted to take on the risk/reward options that may be presented on the tee box.
In any case, while there may be "easy" tee shots and "challanging" tee shots, I think the level to which any tee shot (heck, any shot for that matter) can be classified is going to be dependant on those two factors, first and foremost.
To cite this specific example, in regards to the hole Tom's quote was referring to, I found it a great hole by evaluating it by the two standards above: (1) I was playing from the correct tees in that the 260 carry was at the limits of my abilities, and the hole also presented itself with other easier and perhaps more smart options than taking on the obvious risky shot and (2) the only reason I went for it was because I had been driving the ball well that day...if I couldn't keep a driver in bounds, I would have bailed out left with a 3 wood or iron.
By Tom's quote, he made it sound like a no brainer, but I don't agree. I had to stand on that tee and ask myself: where is the best spot to play my second shot from? Is there a good enough reward to going for it? CAN I pull it off if I do go for it? Do I feel good enough about my game to take on the risk? Am I a better chipper or mid-iron player? etc. etc.
I labelled it the best hole I've played in awhile because it's been awhile since I had to stand on a tee box and THINK (just as you claim to not have to do often at the courses you play). And I believe THAT is what makes a good hole.