Two issues causing the confusion on TD9 / Ian future track:
1) Where will the true center form? East where the LLC is currently located or west where the moisture center is and the direction the shear wants it to go.
2) How strong will the front moving over the NE US will be in two days after the run across Cuba? A weak front draws Ian NE across FL, where as a strong front keeps Ian in the gulf.

This one is going to be dicey for awhile. Model guidance covers a wide range of possibilities from as far east as the western Bahamas to as far west as the FL/AL boarder. Of course the official forecast (for now) is right down the middle near Sarasota. The path is very Charley-like

the upper level pattern ahead will allow for intensification once it consolidates, so this could spin up quickly once it gets into that more favorable environment.