case collapse
It appears to me that you are trying to crimp the case before the end of the case gets to the cannelure. The mouth of the case needs to bend into the reduced diameter at the end of the shank. That case would be a little longer than the others so it wouldn't have anywhere to go as you reached the most powerful part of the lever-throw on the press. You MAY have not felt any increased pressure. Especially if you were working the handle quickly.
The first step would be to standardize the case-length of ALL the cases, not just check them against max-recommended. If you're going to crimp, make sure they are all the same length.
The next step is make sure that the bullet has a place to crimp. You've done that. You did that when you chose that bullet. Someone mentioned seating the bullet "off the rifling." You're at the mercy of the bullet-manufacturer for that measurement, if you want to crimp. If you want to change the "jump," you can set it(usually done for accuracy) but you can't crimp. You CAN if you make a new cannelure, but ONLY then. "Factory-crimp" dies, collet dies, and pushing really hard don't work! Do it right...or DON'T DO IT!
It appears to me that you're loading an auto with box-magazine.(use WHATEVER terms you wish to replace those words) You're loading to replace factory ammo, so I think you're right, just need to finesse the settings.
The military FMJ that you bought(am I right?) has a boattail, so there's no problem getting it started into the case, BUT it's a LOT better if you deburr after you trim, and maybe even if you don't trim. It's just smoother.
To set the die, put a case into the shell-holder and put the ram to the top. Screw the die in 'til it touches the case, then back it off a little, 1/2-turn or so. Then, insert a bullet into a case and start seating it until the mouth of the case matches the middle of the cannelure. Now back the seating stem all the way off, and thread the DIE in until it gives the proper crimp, just enough to hold the bullet against recoil. It it proves, later to not be enough, turn it a little more...Set the lock-ring. Now, turn the seating stem in until it touches the bullet that's still in the die. Take the next case, and install a bullet the same as before, to see if it keeps the same measurement. You may have to turn the seating-stem in a 1/4 turn or so.
I think using an uncharged case is better, then pull the bullet...but you have your own safety procedures. If you don't have an inertia-puller or collet-type, PM me and I'll "try" to figure something.
Have fun,
Gene