All the years I've been in Cape Town and hiked all over the place, this was my first time up Lion's Head. It was not a difficult hike as about three quarters of the way is a walking path, and only the second third has chains where it is nearly vertical (there is an alternative route that actually avoids the chains) and many families were also on the route. The idea is to go up before sunset on a day around Full Moon time, enjoy the sunset, and then come down. But it is very busy which makes it a bit slower, but also has a great atmosphere and is a lot safer. There were also a lot of tourists who came to do the hike... including some Dutch guys who are carrying a garden gnome everywhere with them. Allow about an hour and a half to get to the top at a relaxed pace.
I mainly used my Galaxy S4 for the photos as well as it capturing the route using the MyTracks app. I used my GoPro action cam for the video shots, and the Google helped out with auto-awesome panoramas and auto-awesome motion shots for the twinkling lights.