By the way my Charter Arms 44 SS Special is proofed to 21000psi lower end and 23000psi upper end.
Ah. Here we have the classic failure to understand that "resists blowing up" strength is NOT the same as "action and lockwork strength".
Any revolver will hold together so long as the cylinder remains one piece of metal. And as you state, the Charters will do that fine.
The problem is, the *cumulative* effect of the frame and action being shaken around will loosen them up. Note: not "may", WILL.
That's simply a fact.
Compare and contrast with, say, a Ruger Blackhawk in...well, any caliber really. You CAN blow one up with stupid handloading, although in some calibers (357 in the large frame) it's borderline difficult. But it's not just the cylinder that's tough - the rest of the gun will stand up too, so we often see old ones, slick as snot, obvious massive holster wear, grips worn out, obviously has 20,000+ magnum rounds through it and it's still "tight and right" and an excellent shooter.
Even the vaunted S&W N-frame 357Mags have the same problem as the Charters, although not as extreme: while they won't blow up, lots of fast fire (even with 38s!) will pound the action parts to scrap as that heavy cylinder starts and stops on inadequate action parts. Which is why in fast-fire competition (PPC) the K-frame S&Ws were preferred over N-frames because the Ks stood up better even though the Ns were "proofed" WAY higher.
Upshot: what the Charter Bulldogs are "proofed" to has nothing to do with long-term reliability.
Personally I kind of agree with Jeff Cooper's statement, "Put not your faith into hollowpoint bullets."
Sorry, but a LOT has changed since Cooper's day as a teacher. Hollowpoint designs have come a long way.
On top of that, the basic shape of the Gold Dot 200 if it fails to expand isn't half bad, down on the Keith by only a bit. So your "gamble" isn't extreme. If you were comparing the Keith .44 250 to, say, a Federal 327 (.32cal) hollowpoint which IF it works will expand to .50ish, well then you have a point - a gamble is being taken with the .32.
But in this comparison, both rounds in .44, the "risk" of an expansion failure doesn't set you back that far.