I just got my sled going after a burn down that was a little hard to diagnose. I assumed it was an air pocket in the coolant system as I had just put the motor together 15 mile earlier. With all new parts- pistons(Wisecos and coated), crank, rods, and bearings(updated). I have to admit I did not now about the nose in the air bleeding technique so......

The second time around I adjusted the oil pump to the 2000-10 spec, installed a new filter and bleed the coolant system thoroughly. I also found an alarming amount of frost around the fuel cap upon filling it for the break in runs. This led me to suspect a burn down assossiated w/ water in the fuel. My machinist said he thought the burnt piston looked like it lost lube. I put dry gas in it and 50 miles later I have no problems. Save shear nerve damage due to my fear of another burn down, or that though I did find and adjust some issues I may not have found the culprit.

It was either air pocket, oil pump setting, frost/water in fuel, or maybe the Wisecos were to fat. Can anyone see my dilemma? Any suggestions?

I see your delima. Wiseco's are most allways to tight if you just install them without honing the cylinders for proper fit...they also like alot of warm up time before you ride. Water in the tank is also a big no no. It will scare the intake side of the piston quick by washing the oil away. Oil pump spec as long as it was close, I dont think it would have took it down that quick.
My opinion, it was a few things, New wiseco's, water in the tank, and possible an air pocket in the cooling system. If they pistons were tight and the sled was not up to temp to open the thermostat, and you created a hot spot on the cylinder(more than likely only one would have had the hot spot) along with the water, you exspanded that cylinder quicker than the piston... and without the proper lube on the intake side, BOOM