First night my wife and I landed up sleeping outside we slept in a local park that I knew. We had come down from the countryside with a few Rands (enough for 1 meal maybe) and had hoped to stay with a friend. He was unable to give us a place to stay, so we had to sleep outside.
After the insecurity of that 1st night I told my wife that we have to find a safer place to sleep, so we climbed up the slopes of Table Mountain (about a 1 hour walk) and found quite a obscured spot amongst some bushes and trees. We cleared it out of sticks and rocks, made it a bit habitable and then went make to the city looking for work. We'd spend the day going from one place to the next looking for work until it started growing dark. Then we'd head up the mountain to our little spot for the night.
Did that daily for a month until we were able to secure a small shack room in the townships, where we stayed for another few months until I get a job offer.
Was my wife's temp waitering jobs that kept us fed whilst I was looking for work.
Biggest challenge was mental, keeping focussed, clean, looking presentable and just making my job looking for a job.