Unless you're going to be carrying OWB, I would just pick up a better quality IWB holster as it sounds like you need one. If you're already carrying there's no sense in practicing in a fashion that isn't how you carry, unless you're looking to do Competition.
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I was shooting Winchester 115 grain brass fmj. It's bulk range rounds bought from Wal-Mart.
I've had this problem before after I switched the magazine release to the right side of the gun. It caused the follower to get caught in the notch for the release on the left side looking spring tension and keeping it from pushing the rounds up. I sanded the edge of the follower to try and keep it from catching. It seemed to help but I may need to take a little bit more off the edge. The magazine hasn't been cleaned but I also haven't dropped it in the dirt at all. My gun is due for a good cleaning though.
I'll print that target and see how it goes.
On the holster, I hope to someday shoot 3 gun so I'll be using an OWB at some point. I would still practice my draw from concealment though.