Why not have your cake and eat it too? Install a 14-50 outlet and add a "pigtail" to a HPWC and plug into said 14-50 outlet. Both problems solved.
Maybe what you said is going over my head, but are you saying there is a way to take a 14-50 outlet and use it to power 2 separate EVSEs? Let's say both EVSEs plugged into the 14-50 outlet (via pigtailing or whatever) could be scaled back to 20A, so max draw would still only be 40A. Is there such a setup?