The filter should be mounted on the left side of the tractor because the right side is the side that has the lift arm for the blade and the blower on it as well as the chute rotator.
It needs to be out of the way when changing drive belts but has to be mounted solidly so that filters can be tightened and loosened. Ideally, the filter canister should hang down so that the oil is retained when the old filter is removed. It should be plumbed in just before the cooler and in a spot where a filter wrench can be used without interference .
All of that is a pretty tall order. I would also suggest that you install an hour meter if you do not have one already and then create a service log. Changing the filter annually is likely overkill for most owners that put less than 100 hours per year on their tractor. After all, Case called for an oil change only if 500 hours was reached within the 12 month period and that was with no filtration.
Any particulate captured by the filter will stay in the filter whether you leave it there for one year or three years. I think that 3 years or 250 hours, whichever comes first, would be the point at which I would replace the filter.