2. Comesa isn't required, it just makes your life easier, as you can buy 3rd party liability insurance for multiple countries at once, for a low price. You should be able to buy Comesa in the first Comesa country you get to. Tricky thing with Comesa, it is effectively a rider on existing 3rd party insurance issued by a Comesa country.
This means when you get to your first Comesa country (Don't know if Sudan is or not, I have done this coming from the south, Zambia in my case) you purchase 3rd party insurance. I'd guess available at the border. Then you can ask that insurance agent if they also sell Comesa. You may have to travel to the office in a nearby town/city to get the Comesa. In my case, coming into Zambia, I purchased 3rd party out of some shack at the border for ~$25USD, then drove 1hr into town to the offices of my 3rd party insurance and for another $40USD (or something like that) I was issued a yellow Comesa card that covers however many countries you pay for. I was always skeptical that it would actually work, but the police are all familiar with the Comesa yellow card and will accept it if they ask to see insurance.
3. Namibia and South Africa, 3rd party insurance is part of the fuel tax, so no extra paperwork required. Botswana, it's a mandatory charge when you cross the border, you'll pay it upon entry. I have had it done by the customs/immigration officers and printed on a receipt, or at a small border post I was directed to a more traditional small office that sold it. It's cheap ($15USD?). Either way, just ask when you clear in at the border and they'll sort you out, it's not a big deal.
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