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I've got a harley oil cooler on my 03 night train. i live in indiana where there are days that it is 100 degrees outside with 100% humidity (nasty stickey hot) and my bike about never get over 210 degrees (i've got a 95" kit in it too). the harley oil cooler has a thermostat so it only opens up once it gets so hot. i really like mine.
I put the HD oil cooler with thermostat on my Softail and it changed my "normal operating" temps from 10-20 degrees cooler than before the cooler was installed. Yes Harleys have done fine without them for many years, but my opinion is it can only help my machine. Heat is the number one enemy of Harleys.
I rode yesterday 2-up with other Harleys, temp outside was around 78-80...we got caught in stop n go traffic south bound on the 15 Fwy due to everyone wanting to go to "Old Town" Temecula. I'm guessing it was 10 plus miles from before where the 215 dumps onto the 15 south..we never got out of 1st gear, duck walked alot until we got to hwy 79 south. Not much air moving through the cooler at those low speeds. While stopped I checked my oil temp with my analog gauge (accurate..tested it in boiling water) a few times we were stopped. My oil never went above 230 degrees, two other bikes were 240-250ish. And once we hit Hwy 79 for 5-10 miles running 45-50 MPH my oil temp went down quicker than guys with out coolers.
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