I can tell you that adding a gain stage to a Princeton can turn it into a flaming monster. I changed the output section in mine to dual 6L6 and converted the trem tube to just one single triode gain stage; you may or may not wish to do that. At the time I did this, I knew nothing about calculating gains, I just pretty much duplicated the first preamp stage and threw it into the chain after the tone stack. My purpose was to create a "pre" gain and a "post" gain. Sounds kind of like what you are contemplating. Well, you could say the gain went up...I did not get the parts values right but that amp was capable of very, very loud cleans and borderline out of control nasty high gain. I really could not turn it over about 3 without forcing everyone out of the room. It was a great sounding amp. Along with the 6L6 change, I used a Dyna Mk IV transformer which no doubt was capable of driving a speaker with extreme gusto, real 35-watt OT.
It sounds like you have done a fair amount of experimenting, more than I, with the tone stack. But what I would say is that if you want loud-clean, louder than how you play in a store, I'd imagine that with your extra gain stage you would be overdriving 6V6's early and easily. And a PR OT is already undersized, which has a lot to do with how much tone you can pump out which would make your super-tone-stack seem more worthwhile.