I'm yet to travel the route, but have done a great deal of research on the matter.
The easiest route being the eastern route: London......, Italy, Greece, Turkey, Syria, Jordan, Egypt, Sudan, Ethiopia, Kenya, Tanzania, Zambia, Botswana, South Africa. The things making it easy is not only road conditions, but also safety, fuel availabilty, degree of general development, red tape, etc. This will also take you through some of the most beutiful parts of Africa. I will be doing this route on a classic Vespa scooter.
From cape town to a little North of Nairobi, it is paved all the way, except for a few tiny bits. From there on, all the way to Egypt, roads get much worse, gravel roads. In Ethiopia your main concern would be mud in the rainy season, otherwise no problem the entire route (much of the mud problem will include trucks etc getting stuck and blocking the road). In some bits between Cape Town and Nairobi, pot holes slow you down to 30 kmh. The greatest issue is mostly ground clearance, which would be no problem with a Jeep. As for reliability, I have no idea how the Jeep scores. The general reccomendation however seems to be to use "tried and tested" rather than new and grand. For instance, in Africa they don't swap parts but rather repair what is broken, this because parts are not readily available. If your car has lots of advanced electronics and such, fixing it may be difficult as neither parts or knowledge will be readily available.
There is without a doubt better options out there. It seems as though the Toyota land cruisers are a favourite among Africans, for instance the 1980's 60-series (i.e. the HJ61).
I can highly reccomend Chris Scott's "Sahara Overland" A route and planning guide. Another highly reccomended book specific for the eastern route is the Getaway Guide Cape to Cairo, overland (or something like that). It is available at the UK amazon, not the American version. I also think that everyone should read Pelton's "The worlds most Dangerous Places", and/or "Come back Alive". It is anything but what you would expect from the title...
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