I will totally disagree with a couple of your statements. First, "The vast majority of the carry rigs people start with can work if people worked with them." In my experience, almost all folks who embark on a lifetime of concealed carry do not start with high quality holsters and belts. It's almost a stereotype that new gun owners/gun carriers will spend hundreds of dollars on a quality handgun, only to turn around and attempt to pack it in a flimsy $29 Uncle Mike's nylon holster on a flimsy one-inch belt. I've seen it so often over the years, it's almost tragically comical. I have been a small arms instructor and law enforcement firearms instructor for much of my adult life, and I can count on two hands the number of guys (or gals) I've seen invest in a top-quality holster and belt combination right off the bat. Also, until you've availed yourself of quality training (not your half-day state-mandated class in order to get your state's CPL/CHL/CCW license), you don't know what you don't know about carrying a firearm daily -- and the sad fact is, most people do not get training beyond what's required for them to obtain a license to carry.
Also, are you aware of just how many folks carry a concealed handgun, yet don't keep a spare magazine or revolver reload (speed-loader or speed strip) on their person? You'd be amazed, and I'm pretty sure, very disheartened.
No, for most people, carrying a concealed handgun is an evolutionary process that goes way beyond "flitting from gun to gun." Your initial statement may be true for a very select (and lucky or prescient) few, but I submit it's the exception, rather than the rule.