As walkalong posted above, you need to do the "plunk test" to set your oal. Your middle reload in your picture (post #1) looks too long, more often then not the shoulder of the swc bullets will be sticking +/- 1/16" above the case mouth.
If your getting 1 case that flares correctly and the next case looks like the 1 in post #1, that's not from the differences in case oal's (typical max oal case differences is +/- 20/1000th's). More likely then not it's from not pulling the handle on the press consistently or short stroking.
When I roll crimp (normally strait walled cases 38spl/44spl/etc) I seat and crimp the bullet in the same step. When I taper crimp (9mm/45acp) I seat the bullet in 1 stage and crimp in another stage.
Crimping is very subjective and everyone has their favorite spotted puppy. Myself I put a 2/1000th's to 3/1000th's crimp on all my 9mm & 45acp reloads. Doing this aids in feeding along with having consistent ignition/consistent short start pressure which leads to accuracy. Everyone talks about the differences in case thickness and case mfg's. Couple that with new or once fired brass vs work hardened brass that's been reloaded several times. The word neck tension keeps coming up in these threads. Just how consistent do you think the neck tension is with all the differences in cases, wall thicknesses, soft/hard brass, case oal's, etc????
The 9mm is a fantastic round that can be extremely accurate & IMHO most factory expanders fall short/are the weak link in reloading the 9mm's.
Most factory expanders are designed for the smaller in dimeter jacketed bullets (.355") and are typically short relying on huge amounts of case neck tension due to the massive differences in cases. A factory expander next to a custom expander that I mde for reloading 9mm's.
Even with jacketed bullets there's huge differences in the seating depths of the base of the bullet. A cut-a-way of different bullets and a lyman m-die expander.
The m-die has a "step" built into it that's long enough to to make up any differences in the length of the cases (oal's). My custom expander has the same step, the only difference is that I beveled the edge on mine. Using this type of expander takes the min/max case oal thing out of play giving the reloader a consistent expanded case no matter the oal or brand. NEO bullet mold company sells these types of custom expanders for little $$$. It would be worth your while to pick up 2 of them. 1 for jacketed bullets and another for larger in diameter plated/coated/cast bullets.
Good luck I'm sure you'll get everything dialed in