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I can only comment on running an 18" on the back of my FXSTB -- although I plan on running 18s front and rear on my FLSTF...
A lot of people who upgrade to aftermarket wheels upgrade to the 18" -- whether in the back on a 18/21 combo or 18s front and rear. Since you are spending those kinds of $$$, might as well as get more wheel to show off -- especially with the rotors and drive pulley in the way -- even though most match those with the wheels.
As mentioned, I ran a 18 X 5.5 with a 180 rear tire. I noticed no difference in handling -- or comfort. That being said, the bike was already lowered and before I even switched wheels, quite "stiff". The 18s would tend to be stiffer b\c you are giving up considerable sidewall -- which acts in concert with the suspension to provide smooth riding -- to the 16s that are currently on your bike.
I would say it is more aesthetics more than anything... Hope that helps.
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