Like you Rob, I am not so worried about overheating, but I would like to see how hot the oil gets (or does not get) in winter and insulate the oil cooler appropriately.
Personally I would prefer the sender to not be on the sump drain bolt incase it got bashed.
I keep meaning to move my OAT probe from wherever it is hidden under the rear mudguard to someplace where it can measure oil temperature…..even just taped to an oil line, to see how the normal’ summer oil temperature reduces in winter.
On slower low hp air cooled bikes I like to know my oil temps, especially where I ride. In the summer on many of my trips climbing a pass is unavoidable, on asphalt and gravel, some a mile of grade and some as much as six miles, some shallow grades with several very steep. On a 85 to 90F day several miles of climbing grades really loads up the poor Himi with the definite possibility of overheating, especially when loaded with my gear. Even my DR had problems on them some days.
I know many don't feel the need or necessity to monitor their oil temp and and that's fine. I personally see the benefit.
The oil probes I use only extend around 1/2" past the original drain plug and they're solid. With a good bash plate it's no more likely to be damaged than the stock plug. I've high-sided my poor old Dakar so many times on logs and rocks it's a wonder the frame didn't break, but never close to impacting the oil probe.
We each have our own preferences.
. I'll continue to live safe in the knowledge that the bike was designed to operate perfectly in a climate much hotter than that of the UK. Mine seems to run fine at low speed, 1st gear & pushing through 6 feet tall grass. Ignorance is bliss 
