Unless both dovetails and tool holders involved have the same fit precision, one holder (the tighter one) will stop the wedges when locked down, the other will not be equally locked because the mechanism for each wedge is bound to each others movement. FIMS has a balancing mechanism that allows three tool holders to be mounted at once for convenience, but I don't think it would work with your typical Aloris/Dorian/Chinesium wedge post.
This is my concern as well. Even when used individually, I can clearly feel a difference in how a tool holder locks in one tool post position versus the same holder locked in the other position. I thought maybe a shim of sorts could even things out but, since I can't actually try it, it's conjecture.