As quick questions go, this is a tough one Josh. Over the years, I have installed two temp indicators. I have the Vapor oil sensor installed in the drain plug and also have an oven thermometer placed into the bottom gap on the back rear of the cylinder head. In both instances what I was looking for was a 'day to day reference' my expectation was to pretty much see the same numbers. Anything out of the ordinary ment conditions had to be out of the ordinary, or something was wrong.
One the lower backside of the cylinder the number that I generally see in the Summer is ( I believe) 300 degrees. Now with the oil temp, since I have a cooler, it generally reads 248. If it seems inclined to get hotter (Summer day and long climb) I will turn on the fan. With the increased air flow on the cylinder my max oil temp seems to be 260. Without the cooler and fan, on a long climb during the Summer, it would seem likely to me, that oil temps would creep up around 300. Hope this helps. Gerry