Long story short, I sent my cylinders to Doug and had them reamed out. My boolits actually fit my cylinders now!.
I'm still having slightly the same problem. If I don't do a really heavy crimp and seat them to Minimum spec my rounds do this in the chamber (see pic).
I reload 44 mag to for a blackhawk and don't see these problems at all. I feel like the case is catching in the cylinder that's why I have to do a heavy crimp. I shot about 20 rounds with heavy crimp and they shot fine and I didn't die so I'm happy. Is it because i'm taper crimping these rounds instead of roll? My 44, 38/357 didn't have these kind of issues with reloading.
Reloading casted/PC 200 gr SWC and 230gr plated berry bullets. Both are same way. Seating casted to 1.225 and berrys to 1.2205