Hi Adam and welcome to, well, here. We did something vaguely similar to your route this time last year (not the deep south or the loop into Canada) starting and finishing in NJ and covered about 10k miles.
If you're heading west about now you'll have no real problem (other than heat) but it gets cold fast if you're going to be up north in October or later. If you do find a way to ship the bike across the mid west post it up here as I'd be interested.
If you're running a blog or something I'd be interested to see how you get on as the deep south and over the border into Canada are probably the next two trips I'll be doing in the US.
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