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It took us 2/3 weeks to find a landcruiser that we were happy with and another three weeks to work with the car and fit it out so we were happy with it. But in hindsight we'd have prefered to work with the car for longer to get to know the vehicle which would have saved some heartache. (Remember to do a mini trip to test everything for a few days - wherever you're based from.) It also took a few weeks to wait for the carnet etc although this coincded with the time we spent in the garage under the car. And your right, accommodation is a pain all this time unless you have some patient friends over there.
We found the car through SA Gumtree which you can check on-line, useful because you can compare prices. South Africa is really set up for overland travel - there is a wealth of experience and shops there - but I think it may be more expensive, particularly for the car purchase. Better to sell there though.
We have some good contacts in CapeTown we're happy to pass on - but the time in getting the car ready is really something to think about, especially that the car sometimes needs to be at a garage for more than a day ...
Depends what car you find as to how equipped it is - but there'll always be things you'll want to change. We didn't find anything which was fully equipped and ready to go. I don't know if that is typical or not.
Alternatively we know of a great land cruiser, ready to go, fully equipped, even has namibian plates making it easier to sell - and you could go from north to south instead. Middle East and eastern europe has some great places and people in its own right!!
Email anything else you need to know - which ever way you go!
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