I own and smoke pipes going ranging in age from 1882 to just a few months ago. I enjoy the different shapes, origins, and stories behind these pipes, both the old British factory pipes and the new Artisan pipes.
Obviously, many of the pipes in my pile are estates, since my favorite British pipes haven't been made in 60 years. Buying on the estate market has the advantage of saving about 50% of the cost, except for a few collectibles where the cost can be pretty steep.
I didn't need or want the women I've schtupped to be virgins, and I've been far more intimately entangled there, so why would I care about my pipes being experienced? I don't bring my own cutlery to a restaurant. For those who are horrified at the thought of putting their mouth where someone else's has been, I suggest you look across the table at your partner and realize that someone else blazed the trail before you, so get over it.
There are also the clear pleasures of being the original owner and/or commissioning a pipe. A number of pipes, all of them artisan made, were bought new and a number were commissioned. There's that extra involvement of working directly with the artisan that makes the result much more personal than buying from a dealer.
As for how a pipe develops, that depends on a variety of things, such as the quality of materials, workmanship and the use the pipe undergoes. I've seen pipes a century old that look almost brand new, and pipes that have had the life beat out of them. Some pipe users are ignorant pigs. Thankfully, when it comes to higher end pipes, most are careful with them.
