Leaking machines, I don't think your going to find many that don't leak some. Most machines have so many lubrication points, and have no way to contain the run off, so to me that's a total loss system. For instance, my mill will allways leak oil, it must have the oil cups topped up on every use. Its a total loss system, so if left sitting for days, it will have a nice puddle of oil on the table. But, clean fresh oil on the table is a good sign . My mill also has a 1-shot oiler for the screws, total loss again. Seems everywhere you put oil in on the mill, its going to come out. I rather be topping up all the oil cups daily, and oiling all the lube points, and having to wipe down the excess that leaks out, at least you know she is a well oiled machine!
My lathe on the other hand is a different story. My 41 Sidney has a full gear head that takes 12-quarts of oil. It has sight windows on the front and back of the headstock. The front shows you that the oil pump is working, the rear shows the oil level. The headstock on mine should not lose oil. The apron on the Sidney has a oil pump to pump oil to the saddle ways, and cross slide ways, and the apron should not leak oil either, but the oil passages where the oil exits to lube the ways will allways be wet with oil. All other regular lube points on my lathe will be total loss, and these are lube points with cups that need to be topped up on a daily basis.
As another poster has said, when you stop seeing the oil, it must mean your out of it. And that's not good! If your not wipeing up oil from the lube points on your machines, Id suspect they aren't getting enough. Leak free machines would be nice, but they need the oil to live a long happy life.