My earlier post was tongue-in-cheek, btw.
I've posed this question in the past, and haven't received a real answer yet.
What is the plan if the oil temperature gets "too high" (probably need a definition of too high)? When it hits that magic number, do you shut it down and sit on the side of the road for an hour or two while the oil cools? To what purpose, since it will heat right back up when you fire it up to continue your ride.
There are some characteristics that should be monitored on a constant basis, but I don't see oil temp being one of them. Oil
pressure is something that should be continuously monitored. Oil
temperature is going to be whatever it's going to be for the conditions under which you are riding, and unless you only plan to ride when the ambient temps are below 70°F and there is no traffic, worrying about the oil temperature is just going to make you nuts. You bought a 1903 design air cooled V-Twin with the rear cylinder lined up directly behind the front cylinder, effectively shielding it from a significant portion of the air flow necessary to cool the engine. It runs hot, and it transfers that heat to the oil. Until someone repeals the laws of thermodynamics, or Harley joins the modern world, that's just the way it's going to be. Bending over at every stop light to push a button and watch a little LCD display just seems a bit much to me, and it isn't going to make the oil any cooler anyway. If you want to do that, spend the money on better oil coolers, better tunes, better cylinders with better heat transfer characteristics, etc. Or you could buy something with a modern engine design, I suppose.

From what I've learned on the subject over the years, regular motor oil has a maximum safe temperature limit of approximately 250°F, and synthetics approximately 300°. Above those temperatures, the oils break down more rapidly and should be changed more often. So if you use a good synthetic oil, unless you see temps of 300° or higher on a regular basis I don't think all the worrying and potential ulcers are justified. If people really must have something to worry about, I can think of a
lot more to worry about with a Harley than the motor oil temperature.
As for the accuracy of the dipstick gauge, it should be real easy to check. Get a lab grade thermometer with a scale that goes to 300°F, check the dipstick reading and then remove the dipstick and insert the thermometer, compare readings. That will tell you something useful about the accuracy of the gauge. Trying to compare your readings to those of other people on different bikes ridden under different conditions doesn't really tell you anything.
Jerry