Greetings!
Answers:
1. I was mandated to carry, so there was no such thing as “knowing” I would be “ready.” My training had been in a police academy, with the duty rig. There had been no training with our concealed-carry rigs.
2. Well, that being March 1984, I am not sure I can remember “one” lesson learned at the “start.”
I remember that I started carrying a 2.5” S&W Model 66, but that I soon gravitated toward concealing a 4” duty revolver, rather early, and have tended to favor carrying 4”-to-5” barreled handguns as “primary” since that time. Now that I have retired, and my mission has changed, it remains to be seen whether I reduce the size of my favored carry weapons.
3. I have been carrying a knife, or two, since grade school, in the Seventies. Carry a knife. Even computer geeks carry knives. Opening tamper-resistant packaging with one’s teeth is difficult, and looks silly. Stout blades, and substantial handles, make it easier to cut precisely, without making slip-ups and errors.
Lights: I favor the Surefire LX2 Digital Lumamax. I have several, and a very nice thermal-molded Kydex-like belt carrier. It has been superseded by newer models, by now, but every Surefire light seems to require a different-sized sheath or holster, so I am not going to change lights for a while.