In regards to hot oil and how it plays havoc with your oil, I went to Hayden's website to see what they offered for oil coolers... By the way, they have just about everything one could look for.
Here is what they say about oil temp and mileage. Now this is for a water cooled motor, but I'm sure the same is true for air cooled, if not more so.
On a side note, back in 2000 I built a '40 Willys Coupe streetrod with a blown 1957 Chrysler 392 hemi. I had an engine builder in Saginaw MI build it for me from my very used engine. When we got to the point of breakin, he invited me to his shop. Actually I don't think he could have kept me away. He even let me do a pull on the motor after it was broken in.
During the warm up he waited until the oil hit 180* before he would put any load on it. He was very direct about temp and said that to perform the best and protect the motor, it needed to be at least 180 and not over around 210. But he didn't say that over 180 he lost power. He ran the oil through a cooler in his dyno room and it never got over 200. I had a cooler on the Willys besides the pan holding 9 quarts of oil for added cooling.
I also ran a Masterlube pre-luber on the car. In fact if you go to Masterlube's website, you'll see my black Willys on their home page.
Masterlube Here's a picture that shows the Masterlube on the front of my Willys with the tilt front end off.
How this works is like this. I had the 2qt system that you plumb into your oiling pressure line. With 2qt oil in the tank you then fill up the top of the tank with air pressure. In my case it was around 80 psi.
With the ignition key on, you lift up the spring loaded toggle switch to release the oil from the tank and into the motor's oiling system. When you see oil pressure on your gauge, you let go and start the motor. As soon as the motor starts you automatically start to replenish the oil depleted from the tank during the pre-lube. At some point during the motor's run time you will hit your max oil pressure, my case this would be around 80 psi. Then you would be ready to pre-lube once again. I would usually not pre-lube if I had run the motor within the last hour or so.
With this you will never start your motor dry. I believe they have 1qt thru 3qt systems. This is NOT an active oil tank that functions while running, but if you had to add oil for some reason you could lift up on the toggle switch and force oil into the system with whatever head pressure you had in the tank as an emergency type action.
The bearings in V-Twins are usually roller or needle style, not babbit like in a conventional car motor. So pre-lubing may not be as necessary as in a car motor.
Sorry for rambling again.