Hi everyone I am new here and excited to be part of this awesome hiking community! I’m thinking about planning my first multi-day hike sometime soon maybe something like the Otter Trail or Drakensberg Grand Traverse but I am open to suggestions on routes that are great for first-timers. Any tips on planning gear recommendations, or must-know safety advice would be hugely appreciated. Thanks in advance and happy hiking
Hey John, always exciting and a bit intimidating! There are some really great general resources (Am a big fan of Andrew Skurka’s writing for this), I would say the other really helpful thing is just finding a blog or trip report from someone who has done the trail you are aiming for before. Makes a huge difference having some sense of the details in terms of logistics.
I’ll throw in things I wish I had jumped straight to years ago.
Blisters and sore feet ruin hikes quicker than anything. Just wear trail runners, they breath way better and water comes out of them, ankle support is a myth 
Rotate a pair of socks at lunch and pay attention to your feet.
Controversially, you probably don’t need a giant medical aid kit, some leukotape p, ibuprofen, stomach meds (Stop things going or encourage them to) and a pair of small scissors will cover 98% of things. Splint and a coagulant agent seems like the next step up.
You will likely have multiple cellphones in any group you are hiking with. Ask around on here for a route track or create your own using something like Caltopo. Outside of the Cederberg and Drakensberg we are not flush with good maps I feel, and have found you almost universally can’t rely on provided maps at parks or the trail markings. Maps are also a pain in the ass in the wind and weather 
A backup compass of some sort can be pretty handy though, GPS is amazing but have found to never be great for just getting a bearing.
Water is often the fiddly thing, its heavy and getting info about water sources can be fiddly. Carry less of other things so you can carry water. Filter your water, everyone loves their drinking from a fresh mountain stream, but the stomach issues hiking is a killer, this always seems like a daft risk for no reason. Chlorine tablets work but you can taste it, just picking up a sawyer squeeze or platypus quickdraw feels like the easiest answer (Try get a Sawyer Squeeze off Amazon with a bladder, for some reason we only seem to stock the smaller one in SA, which works but is much slower. If you look after them they last forever)
Pay attention to weight from the beginning. Everyone will tell you to just go with the easiest cheapest stuff at the beginning to find out if you like multiday hikes. Nothing puts people off more than hauling 25kgs up a mountain on blistered feet. Materials have gotten really good, have a look at Naturehike, Decathalon and First Ascent if you need to pickup some gear. Lighter and simpler is going to win most of the time. You can easily knock a couple of KG’s off your weight by just looking around in terms of tents and bags. Down sleeping bags help a lot but are not cheap here ever.
Clothes are the secret weight issue for a lot of people. Just bring less! What ever you are hiking in, a change of socks, maybe a fleece and a puffy jacket. Rain jacket or backup poncho if not expecting rain. Something light to sleep in is also a nice luxury.
Sleep often seems to be the struggle for people. Your pad determines a lot about how warm your sleep system is, our local inflatable pads are terrible First Ascent keeps getting better but they still are going tiny widths to try keep the weights competitive. If you want to make an investment, sea to summit, thermarest and Exped make good stuff, and apparently Naturehike has gotten decent. An inflatable pillow with a buff around it is great, earplugs can be life saver (I like the silicon swimming ones for sleeping).
Trekking poles are amazing. I’ve seen them save hikes for people and keep people from getting injured dozens of times. Just look up how you are actually meant to use them.
Will take you a while to work out how much food you need to bring. You are going to over-pack in the beginning Tend to find people go for way more than they end up needing. Progressively I’ve gotten simpler with food over the year, anything that can be made with boiling water in a bag wins out. Trying to cook on a tiny gas stove and then clean up pots and pans at night with limited water while not polluting a river system is too much work to bother in my mind.
Okay, that’s my long ramble off the top of my head while avoiding answering emails! Have fun and ask away if you are looking for anything more specific.
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Welcome to the hiking community! Jaxz has given some excellent advice. I think that planning a Drakensberg Grand Traverse as a first time multi-day hiker is possibly biting off more than you can chew. There are lots of shorter routes in the Drakensberg, if you are keen for that area specifically, but do keep in mind that any Drakensberg hike is going to require proper navigation skills. Help is usually very, very far away in the Drakensberg as well. Trails like the Otter, Tsitsikamma, or High Five hiking trail are all a bit more beginner friendly as they have huts for hikers to stay in, and the routes are marked for you so it is harder to get lost. If you are wanting to stay in a tent, you can search online for other wilderness hikes. Piesangkloof in the Magaliesberg allows wild camping on the mountain, for instance. There are also Mountain Club of South Africa properties all over South Africa where you can camp, hike, and climb.
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Ruth also has a really great youtube channel about hiking in SA that would be a good starting point, lots of info on the actual logistics and experience of the hikes over just a travel vlog. Super handy, thanks Ruth!