Plugs tend to be much overthought, I'd say. Except to say that I've never had much luck with the longevity of NGK plugs in any of my British bikes. Sure, that might just have been a string of bad luck, but I'll still steer clear of them now. Some lasted a couple-few weeks, but the last NGK I tried was wacky and stupendously defective right out of the box, with sparks shooting from the threaded part. Never seen that before.
Instead of fussing about with this or that plug or plug type, once that new Champion's in place, why not try experimenting with the throttle a bit on those cold starts? Mine likes just a whisper of throttle after she's been dozing. If it's pretty chilly outside, I'll use the choke too. Yours may like a bit more than a whisper and maybe choke on with every cold start or maybe no choke at all. Neither of my Nortons even had their Amals' chokes installed. Try varying how much fuel you're giving her. Try a bit of priming first (kicking it through without the ignition on) and then maybe none. Try priming with the decompressor engaged. Experiment. That's the ticket for getting her to divulge that "knack."
Lots of times in Britain back in the day I heard guys say, "If you can start it, you can ride it." Such was the power of the idiosyncracies and weird little rituals that each bike had. Yours is no different. You'll get it. Soon it'll just be second nature. It'll also distinguish you from the mass of today's riders, most of whom have never kickstarted ANY bike, let alone a big fussy single.