I own and shoot several Winchester 21's.....the only issues that have come to light has been a couple of 21's that some shade tree blacksmith had been inside and screwed the trigger up. I've been around several people who purchased CSMC 21's and had more problems with them than they should have. These were early CSMC 21's and maybe the quality control improved.
In my humble opinion, you cannot compare John Olin's Winchester 21's to Tony's; the Winchester 21 is an American classic and the CSMC 21's haven't been around long enough to qualify as such. I would rather have a pre-war 21 (or even late 40's to 50's) than a brand new CSMC 21; the Winchester has some experience - some stories it can never tell, but stories I can wonder about. Having said that, if Mr. Cash would like to gift me with one of his CSMC 21's for Father's Day, I would certainly shoot it all summer and next fall and present a full report on the gun in this forum. LOL