Is it always jumping out of the same gear, 2nd, I read a lot of thread's saying there was a problem with the detent spring they broke, you running a stock filter, I don't trust the high flow aftermarket filters, it may change the pressure in there but that's just an opinion not a fact, is it the same as the touring Mobil 1 4t racing oil 10-40w, I ride lately in 95⁰f heat and everything sounds fine, just did a gear oil change, it looked like regular gear oil and smelled like it too, not like synthetic, and I couldn't find the mobilube shc fully synthetic hypoid gear oil it recommended, I called shop they said, motul V-Twin 75-90w they use, I like Mobil products, just a preference, I heard on here someone said Mobil recommended delvac fully synthetic hypoid gear oil 70-90w, sounds a little better now, at low rpm's it did seem to grind a little before and vibrate the floor boards more. I have 44,000 miles on it, 2nd owner just got it, doing a lot of PM cause not sure what was and when done, but I think the gear oil is supposed to be changed every 20,000, I'm going to change it in 500 more just to clean it out a little, and I have a gallon of it.
The coolant is supposed to be changed every so many years I think, but I just changed mine, used Peak Final Charge Global, had all the requirements OAT formula, be careful with the bleeder bolt, I dropped mine behind the oil tank and tried for like 2 hours in 95⁰ Sun and it's not magnetic, I learned to put a little clay bar in the socket to keep it from falling, have no idea where it is still, maybe when I adjust the TB's I'll find it, a new one with washer is $7, I still have a steel one from auto parts store in it, have to change it. I would guess the high temp light's not coming on, Did you check the temp in tuneECU, I think they run about 200⁰f a little more, thermostat is 190 I believe, but that's not a fact either not sure I'm sure someone here knows what's normal, I would think over 210 is high don't know when light comes on, 212 at sea level is boiling but it's a coolant so I guess you can go a little higher than that before it boils and build's up pressure. Well good luck with it