I have the oil cooler on my Glide and I think it may make a slight difference in heat generation. After all, the bike should be running a little cooler and throwing some of the heat out of the radiator.
As for the engine fan, it will take some of the heat off your right leg and throw it onto your left leg. Nobody has much good to say about those fans. There seemed to be a problem with the mounting brackets breaking on early editions. Hopefully that has been corrected.
On another board we are having a discussion about the use of fiberglass header wrap on the exhaust pipe to shield some of the heat. Also seems to bee some good reports about having the exhaust headers ceramic coated at HPC.
Ken