I'm not certain what bikes you are trying to compare, but I made an assumption and looked at tires sizes of the 2017 CVO Street Glide and the 2018/19 CVO Road Glide to keep this as close to "apples to apples" as possible. Harley didn't take the usual route when they went from a 19" front to a 21" front, with a lower aspect ratio tire for the larger rim. The 21" is the same width and aspect ratio as the 19", 130/60. So in this case the overall diameter of the tire does increase by 2" but the width remains the same. I could be wrong, but I think I read somewhere that Harley made changes to the front end on the 21" bikes to compensate for the larger tire diameter.
D408 130/60 B 19 O.D. = 25.39"
D408 130/60 B 21 O.D. = 27.39"
Where I would expect a big difference in handling and ride is with those aftermarket solutions with the 26" and up rim and skinny low profile tires. When you get into the ultra-low profiles and narrow widths, you don't expect a good ride or crisp handling. At that point it is all about looks, not function.
Jerry