Assuming your weapons will shoot factory ammunition reliably, there are three reasons reloaded rounds will not chamber. One is that the base of the case has been "blown out" so it jams and does not go into battery. The second is the bullets are either too large in diameter and/or the nose profile hangs up in the throat of the gun. The third, which I have never experienced, is the case is too long and does not headspace properly.
I do not consider over crimping, as that is so obvious and easy to fix that is does not merit much discussion. Learn to apply a good taper crimp.
IMO a case gauge will (should?) determine if the case is "blown out", or the bullet is too large.
That can be determined with a micrometer as well.
The max diameter of the 9mm case is .391" and tolerance is -.007" If your cases measure more than .391 you need to "bulge bust" them or scrap them.
The maximum diameter of the case at the case mouth is .381" max. and tolerance is -.007". If your cast bullet is oversize, and expands the mouth to over .381", you will need to reduce the diameter of the bullet. If you have an undersized chamber (use Cerosafe to check it) return the barrel or have it reamed to specification. BTW, if you have an oversized chamber in a gun, it could be "blowing out" cases and creating a problem in other guns. Get that barrel replaced.
A case gauge will not tell you if your bullet profile is a problem. Issues with bullet profile can sometimes be addressed with shorter COL, changing to a different bullet that is more forgiving, or having the barrel throated.
I agree with you, having a specific bullet or seating depth to match the issues of each weapon is not an ideal solution. It goes against my KISS philosophy. My reloaded ammunition should be as good or better than factory, therefore it should work in every gun.
I used to have four lever action rifles and four pistols that used the same .38 Spl load. I may have been lucky, but it was convenient not to have to worry about which load I needed for which gun when heading out to practice. Currently I have three 9mm pistols and two 9mm carbines that use the same practice load. Easy-peasy.
9mm brass is too cheap to mess around with. Sorting brass after every range session and having a load that will work with one lot of headstamps but not another is silly IMO. If you have some bad brass, sell it or scrap the offending headstamps.
Your expectations are reasonable. Do not listen to advice to tailor your loads to the gun. If that was required, factory ammunition would be a nightmare and we could not fight wars. You are not creating benchrest ammunition. KISS