So I think I’ve found a more feasible solution. I have two identical “Lipo charger basic” (Tiny little red lipo 500mA chargers that have battery out terminals. This eliminates the balance charging problem. I’ll run power in parallel out of the Bat terminals using rectifier diodes to ensure there’s no accidental push-back voltage. I’ll run the combined 3.7v (4.2v) out to the Lipo Shim to power the Pi ZW, the Powerboost 1000 to power the Zero4U USB hub AND to the Smakn SBT4312 to power the display board at whatever minimum voltage I can get that to run without it bugging out on me. I’ll throw in a power switch right after the diodes, as there’s no way I’ll be able to run AND charge at the same time.
I have no idea how long 4600 mAh is going to last in this configuration, but it’s worth testing to see. Now I just need to wire it all up and see what happens!