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It's air cooled and you have little control over the temp. I run synthetic oil and enjoy the time riding instead of throwing $$$ into the bike and losing sleep at night worried about my engine melting. Having said that my stock 08 Heritage and the wifes stock 08 Deluxe average between 205 and 230. Stuck in stop and go traffic they'll get up to 250 on the oil temp gauge.
Around 250 at the heads is a reasonable operating temp. Some like to run oil coolers, lower afrs to drop it lower. It certainly makes it more comfortable in stop and go traffic and can't hurt. Around 280 you need to start getting concerned and at 300 you need to shut it down and let it cool off. Oil temps? I'm not sure how that compares to head temps.
My 09(96 inch) ranges around 250-265 on hot days. Dealer said I could posibly see 300. If mine gets to around 290-295, I'll shut it down. My 88 inch stayed around 210-230.
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Let's see now, if you get a 20 degree temp reduction from synthetic, another 20 degree from an oil cooler, 15 from a Stage 1, and another 20 degrees from a properly tuned fuel mgmt system your oil temp should be about 150. What a bunch of horse feathers! FYI my owner's manual says that 230 is the normal operating temp.
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