I thought I would just throw this out in case someone has a similar problem in the future. This was kind of a freak occurrence, but it's possible someone else might run into this. When I bought my TW it had a leak that made a mess on the crankcase. I did some checking to find out what it was, then determined it was probably the dreaded base gasket leak. Since it wasn't leaking too bad, just enough to make a mess, I continued riding the TW until I could round up the parts and the time to change them. One day I was riding, and when I stopped I noticed a significant amount of oil dripping off the crankcase. It was evident this was now a pressure leak. After getting the bike home I determined the oil was coming from the right rear of the cylinder. This, of course is where the oil feed to the head is located. So, I bought the parts and changed out the base gasket. On startup, oil was still pouring out. Upon closer investigation (I had to look pretty close), I was able to determine the oil wasn't coming from the base of the cylinder, but from the seam between the crankcase and right side crankcase cover. After pulling the cover it was obvious what had happened. A prior owner had removed the crankcase cover, and when re-installing allowed the gasket to sag. It was just enough to seal until a nice warm day and some spirited riding caused it to give away. The area where it gave way is right where the filter resides. The problem was easily repaired, but this could've been bad had I been way out in the boonies when it gave up. The moral of the story is to always hang the gasket off the dowels on the crankcase, and be careful while installing the cover.
I hope this helps someone down the road.
My handle is B-dub, I ride a T-dub, and drive a V-dub.