I would trust the CLT connection over the MIA but not by much and particularly, not at that time of year. We sometimes connect from HPN thru CLT, and often on the smaller AA planes which I think land on the outermost parts of the CLT property. (Or maybe in VA somewhere?? 😠😠)

One trip I swear we walked a mile between gates and terminals, and thankfully, our SXM AA connection was late. We would NEVER had made it if things were running on time that day. And though not the customary situation, returning can be even worse when you take into consideration US Border Control and claiming luggage and rechecking and all.

A wheelchair porter said flights to and from CLT are often delayed or missed because of this but in honesty we don’t fly that route enough to know from personal firsthand experiences but I do know I wouldn’t take the chance.