IF a system is properly engineered, and not just some sleazy attempt to make a fast buck by bending a cheap bracket to hold an off-the-shelf fan intended to cool things like computers and then mount it to the lousy cooler that comes stock, then I would say an oil cooler with a fan would be a great improvement. Consider if you will the radiators on a modern automobile with thermostatically controlled electric fans. That system has worked great for decades. But just adding a cheap fan to the undersized Harley cooler isn't likely to do a whole heck of a lot. I'd recommend buying a much better oil cooler first, if you really think your oil temperatures are too high. Then avoid sitting around idling for extended periods of time, like when you're stuck waiting for a train to pass or behind a ten mile long line of stopped cars on the freeway.
Jerry