In my opinion, any oil temps over 230 is NOT normal! These new HD are set so lean at the factory to meet emissions, with cams designed only to meet the current standards, they can only run extremely hot.
The problem as I see it is not necessarily the oil temps, but the extrem cylinder head temps that result from the lean burn and emission cams. Head temp at 300 oil temp will be over 500 in worst case, no oil will save you valves/ springs/ rockers under these conditions. Your engine simply won't live long under these conditions.
It rediculous that HD has to bend to these stupid emission standards, but have decided not to argue with mob mentality of US govn't.
Anything that must be done to lower oil temps to reasonable levels will ultimately make the engine last far longer.
Alterations to the exhaust (get rid of the cat), a free breathing air filter, and most importantly, installing a solid tuner and getting it professionally retuned can solve 99% of the issues. A proper sized oil cooler will defintely help too!
JM2CW twinotter