There seems to be a general consensus that doing the same thing over and over, no matter what it is, eventually isn't very helpful in gaining experience (the 1 hour 1000 times comment is right on). I think something else that should be considered is the fact that perhaps a pilot with 1000+ hours has had the opportunity to do a number of different things. One could probably assume that the pilot who has a bunch of time didn't get ALL of it doing the same thing over and over, whether that's 100 dollar burgers, CFIing etc. Perhaps in one's time teaching they had the opportunity to do other flights. I know that when I was CFIing I did a lot of flights for people who owned their own planes and had ratings, but wanted to fly with someone (or wanted to go just one way)...once you get a good reputation chances like that come up. And I think the more time you get, the better the chances of that happening and the better chance of you doing something that might get you some useful experience!

RIGHT RUDDER, RIGHT RUDDER!