Does the landing gear raise smoothly? If yes probably not an oil issue. What could be happening is as you are lowering the front of the trailer the weight of the trailer could be causing the Pilot operated check to chatter open and closed. This could depend on the weight on the landing gear, ambient temp, etc.
This is based on the assumption there are P.O. checks on the landing gear.
Better explanation of what is happening:
The weight of the trailer tongue is heavy enough to collapse or retract the landing gear without any pressure( like lowering a FEL). This causes the loss of pilot pressure to keep the check open. The check closes, pressure builds and opens the check valve, pressure falls, the check closes, etc..
Does your landing gear have a valve for controlling the rate or speed at which the gear moves? If yes possibly try adjusting this a little to slow down the retract speed. Make small adjustments since to closing this valve to much will cause the pump to go to relief pressure and create heat.
Roy