I installed the HD 6 rows oil cooler . most of the rides in open road it will be 200-210 . but when riding in hot weather about 95F 35C , at slow drive or on hill with curves , it came to 250F . but this is rare .I've thought about that Ilan, but then you also have to consider the issue of keeping moisture out of the electric fan, thus ruining it.
Do you know what kind of oil temperatures you are running now? And are you using regular oil or synthetic?