AQIM in southern Western Sahara or Mauritania beheads this jabroni if he makes it that far. Morocco is generally safe for me, but I can grow a serious beard and my French is good enough to get around. Once he is south of layouune, he's in Moroccan wall territory and the AQIM bandits will basically just kill him and take his stuff.
If this journey was plausible, he would do all of the following:
1. Use a land cruiser. It's the only vehicle durable enough for much of the journey. That jeep will last under 8 hours on road surfaces less adequate than hard packed dirt.
2. Always have a companion. Given the range of regions, he needs to rotate companions. In North Africa, he needs someone who speaks Arabic. He may even need to rotate more frequently to have a companion that knows local tribal language. In the south (especially Zimbabwe) his companion needs to be local and black. At all times, the companion needs to be armed and act as a bodyguard.
3. Supplies. He needs to carry at least a day of fuel and a day supply of all other car fluids. Same for most parts. Minimum two spare tires and wheels. Should have at least a week of food and water. Maybe two.
4. Cash. Lots of countries means lots of currencies. In most of those countries, a gringo in a fancy car is a big mark. Getting the right palms greased with the right amount of grease takes a good measure of skill. Number 2 could come in handy here.
5. Travel documents. Given that that nerd is driving, timing is an unknown. So he can't just drop by all of the embassies before leaving his home country and get visas all lined up. That means he needs contingency plans for this (along with extra grease - see 4 above) and likely someone back home that can troubleshoot on short notice. My guess is that the out of pocket cost for travel documents that will work is north of $25 grand. Someone that stupid can't have $25 large sitting around.
6. Guns. Lots of guns. He and companion need to have side arms on their persons. Need something high caliber in case you need to stop a large, angry wild animal in its tracks. Also a good idea to have something that looks threatening and is not 75 years out of date like an AK.
All of those things give this moron a shot at both survival and completion. Still, I put him at being found beheaded with his balls in his mouth at the hands of AQIM somewhere near the Western Sahara - Mauritania border.