New Speedmaster and Bobber are great bikes. As I have a new Bobber, had an America and currently still have an old Speedmaster, my thoughts are as followed:

Selling the bobber next year using the money for a 1100 ccm Kit on the old Speedmaster. The there is power, brakes and groundclearence which is the main problem of the new Speedmaster and the Bobber. Everything else is much better on the new bikes.

So it has to go, I do not want to stash it, but I do not want to crash it either. If you want to go fast, stay on you old generation Speedys and Americas or go for a new Thruxton or T120. But not the Bobber and especially not the new Speedmaster.