Not tryin' to sound like I know anything, because I don't really, so I'll just repeat what I have heard before, and what I think Raby is saying, in different words: these engines are AIR cooled, not OIL cooled. I do believe it will be possible to cook your heads/valves to a very bad result while keeping everything in the sump within "noraml" range. And if you want to get down to cases, there will be a rather large temperature gradient through out the heads while operating normally. Closer to the combustion chamber will be hotter than farther away from it. Also, within a given head, closer to the exhaust valve will be hotter than farther away from it. Exhaust valve seat will run hotter than intake valve seat. You want to get even closer still, there is a gradient in temperature just going around the exhaust valve seat, because there is no symmetry in the structure: some parts are closer to the fins than others. Just the nature of the beast. So there really is no specific, constant "head" temperature. What you do is measure the head temp at some convenient place on an engine that is running "correctly". Then, you assume that all the other temps through out the engine will rise and fall in like manner with this point measurement. Then by some magic (or in Jake's words, after he massages the data) you decide what is too hot and what is OK.
If something changes in the engine to alter the heat flow, and the normal thermal gradients, then there may be hell to pay -- or if not hell, then the mechanic. Case in point: If you develop a slight unseating of the cylinder to the head and so get the tiniest bit of blow-by where the two pieces should be in good thermal contact, the temps in that area of the head are going to change dramatically, while overall, just about nothing else will be noticed: oil temps just fine, and engine running like it always has, or not so different. But right at that spot, temps are going way up. If that spot is, say, right near the exhaust valve, then the seat will heat up in a little place, and when the valve sits there a little while each cycle, it will not cool like it is supposed to. Pretty soon this little part of the exhaust valve gets too hot, and the metal starts to melt, and the valve burns just in this spot. THEN you notice the trouble. You might wonder how I know this. I still have the exhaust valve w/ the little pie-shaped piece burned out of it . . .
Again these are air cooled engines that depend on a considerable amount of heat conduction through the aluminum parts and the fins. The parts you really care about are a good ways removed from the temperature of the oil. Not saying you can't cook your oil, cause you can, for a whole bunch of reasons, so it is good to keep oil temps from going too high.