Building on what Mark has mentioned, I think it's important you come to terms with reality. Your Plan A should be something which is possible today. Let Plan B include Sudan in case there is a rapid conclusion to the conflict.
I would also be looking at West Africa. In recent years Burkina, Mali and Niger have become problematic. I'm not sure if entry is impossible or just inadvisable, but it would only take one more country now to cut off the overland route.
Countries like Nigeria, Gabon, Cote d'Ivoire and I think Angola can be problematic in terms of getting visas on the road.
The FB overlanding groups are good places to get up to date route information.
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EurasiaOverland a memoir of one quarter of a million kilometres by road through all of the Former USSR, Western and Southern Asia.
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