Nick-
I always try to close the triangle at my release point. The OLC scoring algorithm then has the most data points to calculate maximum triangle size. Your southward trip to the clouds would be included in the flight, so the extra leg PROBABLY would not have made any difference. I have tried to "out think" the OLC calculation by using SeeYou to pick other points that might exceed the OLC measurement, but I have NEVER been successful at coming up with a longer distance or larger triangle. As Tom noted above, the finish point must be within 1 km horizontally and no lower than 1 km below the start altitude. Unless you are regularly towing to the Moon, it is hard to finish 1000 m below release altitude. I try to make a mental note when I release and end my flight very near to that point. So far, it has worked for me.