On RS1400 (a different Yanmar tiller) I tipped the unit and let the oil run overnight from the top gearcase down into the side gear area, while that drained into a pan.
I suspect on yours the lowest bolt is drilled all the way through and serves as the drain.
And - I was promised my tiller had fresh oil in it when I bought it from the VN importer. I drained it anyway and it came out milky, a water/oil mix. Next year I drained it again before using it, same result. I wonder if its older cast iron gearcase creates condensation problems.