I know there have been plenty of good ones out of Who Made Who cows, but you are sure injecting a chance for serious front end troubles on females out of that potential mating, particularly when you plan on going back with them. In my opinion, there are better choices with less risk.
You originally asked if some of those types of crosses (i.e. Milkman x Meyer) worked both ways. In my opinion, they often don't. Most high end Milkman steers are coming out of smaller framed cows, which you probably would not get out of a Meyer mating.
Purebred charolais cows work very well with club calf bulls, but your risks (what tends to go wrong with any Charolais cows - not specific to yours) are calves that are either too big (frame) or too hard made. That's what you need to mitigate. I go two ways with cows like this in my own herd when I'm trying to breed replacements: breed them to a HooDoo bloodline purebred/high % bull (to keep some purebred or close to it females - George, Troubador, or such) or breed them to a high % Maine bull to get replacement females (Cerveza, Escalade, Ali sons, etc). Another option that is combination of these two is Yellowjacket - his females are starting to raise some barn burners. Whatever your end result is, you go back on it with something from the Heat Wave line to produce steers. Those bulls will throw all the belly and look you need.