21" no issues other than stock fender may need to be raised. And cornering is NO problem with a 21". Look up Tail of the Dragon, Back of the Dragon, Dragon's Claw, etc and I have ridden them hard with a 21" and went faster than most 19" Road or Electra Glides. Can't speak to 23" from first hand experience. See my garage for pics.
BTW, welcome to the forum from Maryland.
Blessings, Zinc -
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"But when I leave I want to go out like Elijah, with a whirlwind to fuel my chariot of fire." Rich Mullins