Welcome to the madness.
To start YES you do bleed drum brakes. Try running some new fluid through them or check the shoes to see if they are worn. Also check to see if your power assist works by pumping the pedal two or three times then start the engine while holding the pedal down. If it drops down more once the engine starts it should be operational.
A four inch lift can be had from BJ's offroad www.bjsoffroad.com
they have alot of good stuff for wagoneers.
My suggestion would be not to exceed 31" tires with a 4" lift, but that's just me. I plan to go offroad and want the travel. You could probably fit 32" if you wanted.
1997 ZJ 5.2L V8,K&N AIR FILTER,FLO-MASTER EXHAUST 2"BB LIFT 30" REMINGTON WIDE BRUTES. ProComp ES3000 SHOCKS, CUSTOM SPARE TIRE CARRIER AND ROOF RACK,HELLA LIGHTS. JUST GETTING STARTED!!!!!
1968 Jeep (Kaiser) Wagoneer, Buick 350 V8, Isky cam,HEI ignition, TH400 trans and completly stock inside and out.