I have a Woods tiller that has a similar bearing leak. It is a very slow leak that first appeared when the tiller was new. I clean the grease around the bearing every season to see how much/if it leaks. It seems to leak much less now than when the tiller was new. This bearing is on the main tine shaft and would be a lot of work to disassemble to check the gasket. I just deal with it and keep it greased. One thought is that maybe they applied too much grease from the factory, and this excess grease is working its way out. Time will tell. Just keep a watch on it.