I don't know that one actually handles better than the other, but the larger diameter wheel on the Custom makes it more sensitive to road surface irregularities. The fatter, smaller diameter tire of the Classic is more stable. The Custom tends, I believe, to dive into a curve or turn a bit more abruptly than the Classic, where the Classic is a bit smoother going into a curve or turn--leans and rolls more predictably, IMO. But as for overall handling, both handle very well in my experience. To me, the Custom is best suited for a profiling riding style, although I'm sure it tours just fine. The Classic is much better for long distance riding and touring as it seems to be a bit more "planted" on the road.
We have both a Custom and an LT in the family and were having this conversation not long ago -- my Custom "feels" lighter and easier to turn or, perhaps, easier to lean into a turn than my dad's LT. This is even with a MS batwing fairing on my Custom. There's a good bit more mass associated with the Classic/LT tire that plays a role (I'm not sure of the weight differences, if any, between the rims). I agree that the LT feels more "stable" -- and the tire/spokes combo should certainly be able to absorb bumps a bit easier.
However, seating position and handlebar width/angle will matter greatly too in terms of the leverage applied to the bars for turning... as will rider weight and any other accessories like bags or top cases. I came to the Custom from a Ninja 500, so am used to (and I like) the slightly "lighter" feel of the Custom, as well as the flatter bend of the handlebars.
I think the question on tires has been answered very well.
But, I want to point out and agree with Steve here.
The handlebar width/reach will make a huge difference in slow speed maneuvers.
The wider the grips and further the reach; the more body movement you will need to make the same turn.
My Classic LT had wider bars and further reach than my buddies Custom.
Typically, skinnier front wheels will be easy to lean into turns and handle 'quicker', but the trade-off will be stability. Essentially, the fat front tire resists the leaning a little more, which means in rough pavement you won't even feel it and on the superslab it'll track very nicely, but in the twisties you'll be pushing harder and reacting slower than a custom. And vice versa, with the custom fighting over rough pavement or tracking a little looser, but being more 'flickable' through the turns. The skinny tire will also 'follow' grooves in the pavement, where as the fat tire will just barrel right over it.
Plus the fat tire looks WAY better than the bicycle tire that's on the custom. And you don't have to use a bell and a pink basket!
LOL, just kidding I think you'll be happy with either, whichever you think looks better!
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