Your best bet, is to make sure you have a good stock of "Fiches",
Piece of A4 with all your details on, Plus Photo, it makes it a lot easier through Customs and checkpoints.
I have Driven that Route 3 Times now, and found them a Godsend...
If You only Travel by Day, either by Bush Taxi etc., you really shouldn't have to much of a problem. there are plenty of places to stay, all the way through..
Just make sure you carry your Docs, Passport etc, on your Person, and of course Money..
All the Borders are about the Same, Senegal can be Very Hassling at Rosso Ferry, but hey, your in Africa....
Hope that Helps a bit..
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