I think if I were doing it, I'd loop the opposite direction and start on the Gunflint.  Mentally, I think of the section that runs up the Falls Chain to McEwen and then back toward Agnes via Glacier/Louisa as "downhill." This has appeal to me when loaded heavier at the beginning of a trip.  The down side of this option is that it puts you on the Man Chain nearer Labor Day when it is almost certain to have more traffic.

dd