All of those watches are one that I've bought, restored and then sold on. I don't 'do' other people's watches as I'd still consider myself an amateur and wouldn't want the responsibility/liability of handling someone else's watch!
Here is how I make my custom drills: http://jamesriser.com/Machinery/MakingCustomDrills/Spades.html
By starting with HHS I can skip the hardening process and possibly warping when using O-1. I prefer to step down from a standard diameter to the required drill diameter. This makes for a stronger drill and one easier to mount in the lathe or drill press.