This is something I wanted to do with my old crewcab and didn't have the space/time/justification. I'm jealous

One of the Fast & Furry movies had a six wheel crewcab with a flatbed, soooo sexy.
Some thoughts: I looked for but never found a slave cylinder, to slave the tandem axle to the middle one.
Failing that, you could certainly tee the rear brakes together. Discs take more volume to activate, if memory serves, so a disc/disc master might flow enough to do four wheel cylinders. It might also generate enough pressure to send them to Guam, so an adjustable inline valve for the rear circuit is probably a good idea. You might also want to bump up the rear hardline one size (if factory is 1/4", go to 5/16" or 3/8".)
I suspect you'll do a lot of Googling and prolly find better results on hot rod sites, as they're the people doing totally custom brake setups and mixing and matching parts.
Oh, speaking of switching to hydroboost, I've done it on multiple trucks. Well worth it, but you do have to swap a bunch of parts (brake pedal, booster with pushrod, and the master, regardless of disc/disc or disc/drum, has to be for a hydroboost and not vacuum as the mating is different.) Lots of good info in this thread
https://ck5.com/forums/threads/illustrated-hydroboost-swap.306221/
Wondering how you're doing the suspension? Leaf springs for both, one set inboard of the frame, maybe? Links? Inverted leaves like the semis?
Also curious how you plan to drive the tandem -- divorced 205 or the like?
-- A