My path: I recently bought both WA33 JPS Elite and 3ES Elite (arriving this Friday). There is no headphone I know for the WA33 requiring more power than what the 2A3s can deliver. That likely being one of the potential reasons for amp designers to step up 2x power and go 300B instead? On the 3ES, it looks like phones such as the SR-X 9000 (mine hopefully arriving end of this month) provide enough of a reason why more power is needed, excluding the 2A3s from consideration.
On the WA33, since I have several less power hungry headphones (compared to e.g. Susvara, which I am listening to right now from said amp) I can appreciate the decision to calibrate the power scale to be more inclusive towards the lower end, and retain some measure of sophistication vs. the emotional drive of 300Bs. My WA33 JPS Elite gets reasonably close to the ethos of my Ayon Spheris III (a $30k tube preamp). The name of the game, esp. with the Elite edition, is not about tube coloration, more about using the tubes to lay out a differentiated sound field (stage is the wrong word, since it includes layering of instruments as well - something solid state will not provide). FYI - just went back to KR HP 274 rectifier (replacing the Takatsuki 274b) which seems to offer greater synergy with my 2A3 KR HPs.