Joash - Sudan, South Sudan, Uganda, and Malawi are probably the LEAST ideal entry points. All are landlocked, suffer from bureaucracy, and have high taxes/fees involved. However, I don't get to choose where I work (well, I do, but only to a point), and my work is based on the Uganda - South Sudan border, where I live. You will note that the vehicle was shipped from the U.S. (Baltimore) to Dar es Salaam (TZ). It is a toss-up between Dar and Mombasa as a shipping destination point, and many in Africa who are experienced (including me) think there are pluses and minuses to each. I slightly prefer Dar because of the way the port is set up and the way the Tanzanian authorities resolve disputes a bit more quickly than the Kenyans when there is a hiccup in the process, but there are a dozen people who would say the same thing about Mombasa that I say about TZ. It really depends on your experiences and your comfort level with where your equipment is headed.
silversand - local commanders still "rent" their men as armed escorts in Somalia and elsewhere. We use private security (except in two very unusual situations) and I'm overall happier working with people who have been "on the payroll" long enough that I understand their motives, capabilities, and weaknesses.