Great post! I was up against the same quandary. I go for a short run in the morning, half of the year in the darkness. I usually carry with a Remora IWB, but it didn't stay put during a run. The only thing that I've found that worked for me is the belly band style holster, which Daddy Warcrimes's post suggested. I'm thinking he'd agree that you'll have to get used to it, but once adjusted, it works pretty well. I later added a 7"x7" square piece of moleskin to the lining at the site of the holster and that mod added a great measure of comfort. The belly band itself provides decent access while keeping the pistol firmly in place on the run. I carry a .45 Shield, which is reasonably flat, and light weight. Not sure about comfort with a wheel gun, but surely worth a try. Good luck.