300 psi measured at the pump bleeder is quite low, but as JMOR said you should be getting some lift. Since its only 300 psi, either something is wrong with the pump or you have a good size leak some place. If you assume the pump is OK, then the leak must be between the pump and the control valve. Not many options here. I'm thinking pressure relief valve or an o-ring under the top cover. I suppose the pressure tube in the tranny could be leaking too, but if it was you would be getting oil out the shifter hole. Pressure relief valves rarely go bad, so I wouldn't jump to that conclusion.
The only thing I can think of is to pull the inspection port off the left side of the hydraulic reservoir (Dip Stick - PTO lever plate) and take a look inside with the tractor running. You might see something with a mirror and flashlight.
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