I'm not part of the old guard, but probably too old to be a part of the new generation. I'm 40, and have been smoking pipes (irregularly) for 20+ years but regularly for the last 2 years. As far as I can tell, a lot has changed in the industry but the passions that drew us to pipes have remained--the feel of briar in your hand, the smell of a fresh tin of tobacco, and the opportunity to be a part of something that has a history and tradition about it.
When I first started smoking, there were many Pipe shops around--and they sold pipes predominantly with few if any cigars. But out of all the stores, only one offered assistance to me and my teenage friends. (Ironically, it was the most elite and expensive of them all.) Because of that, I was mostly at a loss when it came to learning about pipes, tobacco, and the hobby.
Now, I have to drive an hour to the nearest BM store only to find a few dozen pipes and dusty tins of tobacco. On the flip side, however, the internet has become a huge repository of information and instruction. And since I've found these forums, the internet has also provided the community aspect I can only assume was part of the original tobacco shop experience.
In spite of everything that has changed, it is interesting that the same things that drew my grandfather to smoking a pipe is still attracting a younger generation. That's something I hope never changes.