Evilapes,
Been there done that. IMHO you need to monitor your oil temp, period. Find a way to do it. If your oil temps run above 250 deg F, then switch to Mobil V-Twin, Amsoil, or Redline.
Any proven method to lower oil temps below 250 deg F, while increasing performance, is worthy of further study.
As the summer ambient temp increase, your oil temps will increase as well. Your engine is air cooled, and the less air flow across those jugs and heads, the higher oil temps you will get. Lugging around town or running the engine without forward movement (air flow) are conditions that would indicate a need to monitor CC oil temps.
The 110 engines with the factory oil coolers, really need an electric fan, with a start/stop themostat. I expect that to happen in the near future. Until a viable option for that upgrade exists, I would suggest you monitor your oil temp on these 110 engines closely and work your oil selections as necessary.
Hope that helps...
Rob