Having come from a Chieftain Ltd., I could never own an air cooled motorcycle again. I really don't notice the heat from the motor when riding the Challenger.
Euro 5 emission standards will push most manufacturers to water cooled motors to achieve the mandated cuts in pollutants.
Indian 111cui is running hot ?
Test ride the water cooled Kawi Vulcan VN1700 Voyager - than you will learn more than only two things.
1. Your Indian is not only a cool bike, it is also running cool.
2. You could never imagine how hot a water cooled bike could be/get.
3. Since ~ 2014, there is a second fan (factory installed) below the seat of that Kawi to blow away the heat of the rear exhaust - still frying eggs..
4. In normal traffic, the front fan will nearly run all the time - blowing more heat to your legs.
But overall, it is/was still a good bike. Great price/value/fun ratio.