Jim, I've found that Winchester hulls are slightly shorter then Remington. That might give you a little more room to get a better crimp. You can make a little more room by cutting back on your shot charge (if it's a slug, that ain't happening) or you can cut back on your powder. If your using a slug then you probably want to stick with the slower burning powders that take up more space, just cut back on the charge weight a little. An improved crimp will result in more consistent ignition and velocities. I don't mind a little swirl to my reloads cuz I know I'm not lossing shot and my crimps are dished like they should be. I haven't used your reloading setup, but on my MEC, I'd be adjusting the cam to get more crimp punch depth. The crimp starter will determine the length of the folded material for the crimp. Hope that makes sense.
If your loading buck or birdshot then I would make sure I have the crimp closed or slightly swirled. If it's a slug then it doesn't matter if you can see the tip of the slug. Might help to identify one at a glance. Good Luck