First thing!!! REBUILD the slave cylinder. They can suck/leak air and not a drop of oil.
Then the only way I have every been able to get those tractors bleed easily is to pressure bleed them. The Hi-Lo interlock makes them just about impossible to bleed conventionally. The only way I ever got them to bleed just pumping the pedal is to hook your clear line to the bleeder. Put the other end into a can with enough brake fluid to cover the end. This will not allow the slave cylinder to suck air on the return stroke. Then fill the master cylinder up. Open the bleeder just to where it will allow a slow flow out of it. Slowly pump the pedal. Pausing with the pedal up all of the way. You may have to hook your toe under it at first to get it up all of the way. Leave the bleeder open and just make sure the hose in covered with fluid. I have had to pump several gallons through the system this way to get all the air out. IF you use a clean can on the bottom you can recycle that fluid. Once you stop seeing any air bubbles shut the bleeder and see if you have hard pedal. You should.
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Today's Featured Article - Hydraulics - Cylinder Anatomy - by Curtis von Fange. Let’s make one more addition to our series on hydraulics. I’ve noticed a few questions in the comment section that could pertain to hydraulic cylinders so I thought we could take a short look at this real workhorse of the circuit. Cylinders are the reason for the hydraulic circuit. They take the fluid power delivered from the pump and magically change it into mechanical power. There are many types of cylinders that one might run across on a farm scenario. Each one could take a chapter in
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