October is generally a great time to cruise on the Illinois, Mississippi and the Ten Tom. Once past Chicago you should have no Marina issues, but by late October your window will be closing. The days are shorter, so you are slowed down to probably 70 miles per day, so factor that in.
A few calls to the marinas and fuel stops along the way would answer your questions. Me, I'd not do it this time of the year in a "new" vessel. Too many mechanical unknowns.
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