Cheryl, your question might find a better answer on the BA forum since it is (at least in part) BA specific.
For what it's worth I'll give my opinion even though I have no first hand experience. In JNB you have 2 risks with through-checking luggage - luggage failing to make the connection and luggage being interfered with. There's not much you can do about the first except allow enough time either to re-check the bags or for the bags to be transferred. Three hours should be ample for this. For the other risk make sure your bags are as tamper-proof as possible. At a minimum no zips that can be moved around.*
I think your strategy of carrying a few essentials and through-checking the rest is sound. I am pretty sure the Wilderness Safaris rep in Windhoek will see to it that your luggage is retrieved and forwarded on to you.
*Consider baggage wrapping. I bang on so often about the risks to bags being tampered with that I am sure many must think me excessively paranoid. But SA Express (a local airline affiliated with SAA) has just announced that they are offering their passengers a free baggage wrapping service for the next 3 months in order to reduce pilferage. They claim that baggage wrapping reduces pilferage by 70%.