I'm genuinely excited for that day to come. Right now, I'm effectively drinking from the firehose. The choices are so vast that it's pretty overwhelming for the newcomer. I've truly appreciated all of the information and personal recommendations on this website and feel like I've learned a lot more and that I'm more in tune with smoking a pipe, this time around.
I'm also shooting for quality over quantity, now. Even though I'm just getting back into it, I have always really liked Boswell's pipes. I know these don't necessarily represent the highest quality of pipes available; but, I've checked their website thousands of times over the last dozen years just window shopping, and their styles have always really appealed to me. While I have stocked up on an ample supply of cobs for the exact reasons you've mentioned above, I do think I'll be purchasing higher quality (for my budget, anyways: $100 - $200) pipes from the outset, this time around. I don't (know enough to) have anything against less expensive pipes, it's just that if the name of the game is enjoyment, it makes me happier to look at a rack full of pipes that I truly consider works of art than a rack full of pipes that was filled simply to fill a rack full of pipes, if that makes sense. It's in this light that I seek to add method to the madness.
I'm not sure why, but this go-round with pipe smoking feels differently. It feels like it's here to stay, now, so I want to start picking up a few pipes that really fit my eye. This thread is an effort to add some structure to the buying process.