Really all you need is more volume and a vent for the system. You might be better off to use a long turn 90 degree piece of tubing that will stick in the tank closer to the bottom of the reservoir that the cylinder low pressure hose attaches to. This can be installed with a new hole to match the tubing size in the top of the tank. Then put the proper vented cap back in place on the tank as it originally was. Seal the hole around the tubing you add with a good silicone sealant. You will need to make sure the top of the ram is full of fluid which might be a pita but that should fix you up.
Once you have the air out of the top of the cylinder and its hose, the oil should not have air introduced in the system. The reservoir at this point only needs the extra capacity to make up for the volume of fluid that the cylinder rod displaces with a little air space. When you let the box down and the cylinder retracts it allows the fluid to flow back into the reservoir, at the same time the top of the cylinder is sucking the fluid out of the reservoir and into the cylinder. Raising the cylinder the reverse happens.