When you take the two nuts off that hold the tiller to the tractor, nothing leaks out, there is a bearing and a seal on the end of the splined shaft on the tiller. On the tractor end, there is a female splined coupler that engages the splines on the tiller shaft. The tractor end also has a seal that holds the transmision gear oil. Grease the splined coupler where it slides on the tractor shaft and where it couples to the tiller shaft. It's really a simple coupling and is easy to figure out once you get it apart. Still haven't found my manuals, I know they're around here somewhere.
Well I drained and replaced the transmission oil - no problems. I removed the tiller box from the tractor and drained the oil from the gear box. I noticed the PTO area is filled with a white to off white looking grease. Is that normal? It is packed with grease around the opening. I am going to the autoparts store and get some of the same packing grease. I have not run across any issues so far and everything looks fine. I did notice on the transmission drain plug and the tiller gear box drain plug it looked like some clear silicone seal material had been placed on the plug area. Possibly to prevent leaking? I tuned the tiller gear box upside down to drain. There was not a lot of oil in the gear box. I am going to read how much to put back in the tiller gear box.