I'm having this problem with my brand new Shield, it feels like it's hitting a brick wall. I can't even slam it in. Only way to get it in is to lock the slide open.
My wife and I went to the range last weekend and we rented a 9mm Shield. Every time she racked the slide she had this exact problem. Never once did it happen to me. I think it's the way you're racking the slide that's causing it to happen with the first round.
I agree with what you said but the guy guarantees his work and says if any rivets do come out or the holster fails in any way without you altering the holster he will replace it. I did just check out Old Faithful Holsters and might have to go with one of those. I just think the one I suggested...
Check out fightngear.com, this guy makes his holsters out of horsehide or leather with kydex. He only charges $40 plus $10 s&h, that's about $20 cheaper than you'll find any hybrid holster. He doesn't have the mold for the shield yet but he said he'll have it within the next 30 days.