wingmen option is for outside shooting training only
yes i'm sure, i'm a dwarf trainer
Not true. For Jump Shot too. Don't take it badly but are you still sure about that IS pop? Never heard about it (with guards training) and it is unprobable it wouldn't be discovered before.
(maybe there are different training regime in differents parts of world, a bug happens or they changed training engine with new game engine too - just kidding, although one never knows)