Hi,
Indeed you do not come across any Cherokees doing the overland trip. I just completed it with a friend and we only saw in Toyota Hilux, Landrovers and Toyota Landcruisers.
Concerning the numbers it is all fine to travel alone most of the trip. Especially below Marsabit (Central Kenia) there are a lot of westerners on the road if you travel via: Arusha, Dar Es Salam, Lusaka, Maun, Windhoek, Capetown.
The trip between Marsabit and Moyale I would do in a group (no official police guidance needed). Although for this part of the trip it is much nicer to go via Lake Turkana, which is by far the highlight of the trip. But you can only do outside of the rain-season.
As of Ethiopia the road is a bit more intense, but a lot of fun as well. It was safe may-july 2011 when we travelled. We travelled informally with people we met on the road, as in the end you all go to similar campsites.
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Good luck with planning the trip, I envy you for having this a head of you.
Cheers,
Ed
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