First, your son is absolutely adorable, and if he was in every picture that would be just fine with me!
Second, I think I might not have been so ridiculously and overwhelmingly afraid of travel in Jamaica when I was there if I would have been on the back of a bike instead of in a car. I am not generally someone who is afraid of anything, and I certainly don't have problems with anxiety or panic attacks. However, the time I spent in cars in Jamaica was one of the absolutely most panic-inducing, fearful things I have ever experienced! I literally would have to close my eyes to calm myself, and remind myself everyone drove like that all the time, and I was going to be fine. It was crazy for sure, and everywhere too ~ from Mo Bay to Nigril to the mountains inland and everywhere between, not just in one area. We even went in reverse through part of the roads to get to Mayfield Falls (40-50 kph too, not slow), cause the little car was having transmission troubles. I learned that day I wasn't actually fearless!!! But on a motorcycle, seems like it would make a lot of sense and make travel much easier and less stressful, especially with how little room there is on a lot of the roads for cars to pass each other.
I say go for it if you can afford the license, you would probably love running around Japan on a Harley ~ and maybe eventually a Ducati!! Besides, it will make for some fun memories with you and your wife on date nights!