Ben,
I'll start with carry-and-roll. My average Driver distance is about 270-275. The well-hit ones are probably 285. I suppose that would make my average carry around 240-250, and a good carry around 260. Depending on the layout, I can usually count on 1 or 2 drives a round over 300.
To put this in context...with golf shoes on, I'm 5'8 and 150, and I use a 44.25" driver. Obviously, I'm playing against a lot of guys who are 6'2 and 180, who are very strong and can handle a 45" driver easier.
I'm not anything more than average length for a college player. I'm 10-20 yards shorter than the longest guy on my team (Martin Flores, who's a sophomore and has only recently started working out very much). At the Publinks last year, D.J. Trahan was hitting his 3-wood past my Driver. There are any number of examples like this. When Tiger said that college players hit it longer than Tour players, he's right!
Two things it's safe to say: 1) As far as classic courses becoming easy or obsolete, the problem will get worse. 2) The gap between average hitters and long hitters is growing. Eighteen handicappers are hitting it the same length they did 2 years ago...but I'm hitting my best teeshots 20 yards further than I hit my best ones 2 years ago. I'd say it's 10 yards from the Pro V1, 5 from working out, and 5 from my Driver.
It bothers me a lot about how the classic courses are "shrinking", and even more that we have to build 7,500 yard courses now, that make the game less fun, more expensive, and way too hard for almost everyone. I think you can see from the numbers I just wrote how much has changed just in the last few years, and how quickly this problem is progressing!
I should note...obviously, there aren't any 18 handicappers who are suffering from the classic courses becoming obsolete! This is an issue at the highest levels of competition. Ideally - without worrying about sponsorship, golf companies, etc. - I am in favor of cutting back the distance the ball can go. I'm also in favor of letting 18 handicappers use whatever balls and clubs they need to in order to score better, play quicker, and have more fun.