o that it does not takes more than 18 months to do the loop.
If you keep moving 5 months is more realistic.
Everyone has different tastes , but if we were running it again FL to Charlavoy MI would be out return point.
You might consider the Right loop ,(2-3 months max) which is far shorter , in Canada go East thru the canals Rideau , Richeaeau and eventually exit Lake Champain back into the Hudson River.
Done both and found the Mississippi boring and small boat unfreindly , and the Ten Tom pretty , but again boring.
YRMV
FF