When talking about hiking in the Drakensberg, the first thing that comes to mind is the cost. However, you can start off relatively cheaply as a beginner. Nights in the Berg can be quite cold even in summer, and an entry-level, hollow-fibre sleeping bag with a cowl-top should be your priority if you don’t already own one. This does not need to break the bank but look for a sleeping bag with a temperature rating of about 5˚C that should be adequate for all except winter conditions. If you plan to sleep in caves for your first few hikes, you will be able to get away with a good reliable pair of hiking shoes, a warm sleeping bag, some good friends and of course a sense of humour. Remember you can always borrow or rent a hiking stove, pots, foam mattress, tent and backpack, and some hiking clubs or outdoor stores have some equipment that can also be rented.
So you have been on a few hikes and as your skills and experience grow you see that hiking is something you want to keep doing, only then would I recommend you look at investing in extra equipment. Some of the first equipment you will need to get is a good backpack, a ground sheet and hiking mattress, hiking stove and pots and later on a tent, especially if you plan on doing escarpment hikes. Standard running or trail shoes will be good to start off with but you will soon need to get a pair of good hiking boots that will offer better ankle support and protection, and for winter hiking, proper boots is a must especially for snowy conditions.
Some good advice I can give is that you should not rush out and just buy everything the sales person says you will need. Remember he gets commission on the sales and will try to sell you something you might not really need. You can ask 3 different people the same question and get 3 different answers, so do your own research speak to people who hike regularly and remember if you do decide to buy a piece of new kit, buy the best you can afford as it will outlast a cheaper equivalent.
I personally have hiked for the last 30 years and have learnt a lot by watching what others do, especially the old timers, and sometimes their way will work for you other times not. Remember you need to always be open to change, and if something does not work for you, change it to what will work for you.