I posted this in the other thread you asked before seeing this thread...
I went with the Classic as I wanted the 16" front wheel and CC. The rest ... spotlights, shield, bags, cans, taller seat, etc. were all bonuses --though I do prefer the fishtails.
Regarding the different front wheel, I had read that it rode and handled better. I agree. There has been some discussion about what fenders may or may not fit. Based on nominal measurements, the tires for the 16" and 19" wheels are within 1/4" of each other in width and diameter. I would think that there should be just about no difference with 1/8" less clearance.