Gene,
I spent quite a while looking for a grease fitting that fit in that little depression back when I first started flying my -8. Had no luck, so I bought a cheap fitting and filed it down. When I went to pump grease in, it just kept going - that is when I discovered that I was just filling the entire wheel cavity with grease. The next thing, of course, is that it proceeded to fling all that grease back out (there was no check ball in the zirk). That was the end of trying to grease the Van's tailwheel. I ended up going to a tailwheel with sealed bearings, and had no more worries....
Paul