Doable but...
I know of 2 Frenchmen on bicycles who crossed into South Sudan from Uganda (Gulu to Juba) 2 weeks ago. Thing is, they had to fly to Khartoum from Juba: there used to be a boat but it was discontinued due to civil war flaring up again along the way. My bet is that it is impossible to ride/drive all the way overland.
From what I know people DHL their passports to their home countries to get the Ethiopian visa there. Not very convenient but cheaper than flying.
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