As regards circling approaches, the small carrier I work for does 'em quite often, sometimes to cat D minimums....yes, in a wide body jet.
Great fun.
As for training and checking, I've done this for quite some time, and quite frankly, if during the 'checking' part, if the maneuver is not quite done to spec, the 'training' then starts, and another go at checking follows.
Seems like a reasonable approach to me
The idea is to pass the guys, not fail 'em, and any checker who thinks otherwise, ain't worth a hill of beans.
Period.