You and I are exactly on the same page on this, including the 40-year-EE part. So I have a lot of different crimpers for insertable pins in my collection; what's unique about this pin is is that the strain relief crimps not around the wire's insulation, but around the rubber seal.
I don't have a problem with a 50-cent pin, and as you said, the disties have cut parts of reels as well as loose pieces. I've got a pretty big problem with the local BRP dealer telling me the pins are $6 each and that they have one (1) in stock.
I too have bought the big K+S packages of tubing scraps - crazy handy for lots of things, and often you can find the right size for homemade extractors, but not always. I tried a few of the extractors I have around - AMP, Molex, etc. - but the right Delphi tool is only $15, so I don't have any problem with that at all.