For the OP: The first 12 years or so of pipe smoking, I bought around 300 pipes. Nothing too high end, because I usually couldn't wait and save up enough to get them since I was scarfing up fun lower cost pipes that I really enjoyed. Now I love to crack a pistol case (where I store my briars and meers) and just pick one to take for a spin. The funny thing is, during my quest for vast numbers of pipes I got 4 or so 'bags of smokeable seconds' from MM when they were cheap and plentiful. Now I find that 80% of my smoking is done in a cob. They withstand VAAAAST amounts of punishment, are handy as all heck, and I can smoke them outside doing farm work with zero fear of breaking or losing them (easily replaceable).
I love older US pipes: Linkmans Grabow, Older Kaywoodies, Tom Howard, Wally Frank, Mastercraft, Marxman, etc. Oh and I had to track down a Disney pipe, too. lol . I also love Charatans pipes. The fun they had with odd shapes are just fun. I have carver pipes too, Mike Butera, Steve Weiner, Rad Davis, Bruce Weaver, Tom Eltang, Van Erck, etc.
About 5 years ago, my income changed. I saw it coming and bought right up until I couldn't. I am so happy to have what I have. I feel really blessed. It is so cool to see people here with so many nice pipes. There are some I wish I had gotten, but when I went to the Muletown pipe show, I was pretty surprised to see what pipes are bringing in now. It seems to me like there are less and less overall pipe smokers, but it is the older 'one pipe, one tobacco' guys that are quitting. The new breed of smokers take their pipes seriously and shell out a lot of coin for them.
More power to the carvers, but I am not in a position to support that economy, generally. I focus on getting tobacco when I have any money to spend.
As to shapes, I love odd pipes. Almost all the basic shapes are great to me. I am picky about Pokers, though. I like bulldogs and princes, but if you hold a gun to my head, I think bent pipes smoke better. I think that was the older generations way to keep a pipe hanging better and closer to the mouth. Moder carvers make nosewarmers, of which I am not a huge fan.
@Sig Thank you for the education about knives. I have a couple of decent ones, but you have inspired me to maybe search for a decent budget blade, maybe for my son.