One key factor regarding how much Wilma may try to reintenisfy is how well the inner eyewall feature holds up. There is a large outer eyewall evident on the radar which still seems to be in prety good shape, while the inner eyewall seems to have contracted and may struggle to maintain itself for very long. If the inner wind core maintains itself as it emerges over water, it may try to increase more rapidly (though an ERC would probably ensue shortly after that given the outer eyewall). If all that is left is the large outer eyewall when it emerges offshore, the storm would less prone to rapid intensity changes.
I recall the "No-Name" event of 1993 very well... it is now a famous case study for meteorologists. There wasn't anything tropical about that at all... it was basically a mid-latitude baroclinic system on steroids. This scenario will be different. There definitely could be an enhanced risk of tornados with this system, but the details are still unclear on exactly where and when (forecasting hurricanes is a piece of cake compared to forecasting the probability of tornados 3 days out). A lot depends on how strong the system is when approaching Florida and whether it is still generating outer bands or not.
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