Hi Doug, My info shows that 3 different pumps were fitted to the 285 in addition to the single element ones. The layout will be very similar. When you had the aux pump removed did you strip it and inspect it for wear? Wear can take place in the bushings but particularly in the aluminium body around the outside of the gears. Wear here will certainly reduce output and ultimately maximum pressure.
The parts book for the 285 does not show the rectangular filter similar to the size of a cigarette packet only the inclined one accessible through the underside of the centre housing via the three bolt plate. Do you have this type. You may of course still have the square filter.
This would appear to be a filter or reduced intake problem. As a first step, drain the oil and remove the filter if you have that type. Unfortunately access to the aux pump is via the front opening of the centre housing after you have split the tractor.
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