Where you at in Florida? I was born and raised in Tampa area. Moved north years ago.
Anyhow....Here are some viable choices.
Only you can make a call on aesthetics but If you like the looks of it the Hannigan Classic is a very nice sidecar.
The Velorex offerings are okay. I would lean toward the 565 model. There should be a subframe built to mount these sidecars on a late model sportster. You may find earlier versions around but they are not nearly a good as the new velorexes are in many areas.
Check out the lower left hand picture. Bike look familiar? :-)
Our own CSM American Classic is also a good one. These are built with a steel or aluminum body here at our facility. We are a rep for Hannigan and also Velorex.