As Vivo101 has mentioned, getting to the top of Rolands in a day is quite taxing - especially the last bit from the top of Organs to the cave itself. There are 5 caves around Ndumeni dome itself. At the bottom you have the 2 lower Ndumeni caves (offering virtualy no protection from the rain), then you have Rolands cave in the middle and the 2 upper Ndumeni caves above Rolands. So, enough space for 8 people. If you have to split the group due to circumstances (fitness levels, injury etc.) then there are a number of spots where you can pitch a tent after you top out on Organ Pipes pass. The first is a couple of spots a bit to your left when you are standing at the large cairn facing into Lesotho. Just search around in this area for a relatively flat spot. A bit higher up from where you are is a decent spot. Else, you can camp between Castle Buttress and Cleft Peak, next to the upper reaches of the stream is a couple of nice flat spots.
Finding Rolands cave is actually fairly easy if you know what to look for. Firstly, starting from the cairn at the top of Organs Pipe pass, head left and pass just below the little rocky outcrop you will see on your left. There is a stream flowing (mostly in summer) where you will find the last bit of water before you ascend towards Rolands. Now, once you pass below this outcrop, turn further left, so that you walk up basically in the lowest spot between Ndumeni dome on your right, and the escarpment edge on your left. If you continue up this valley all the way you will fall off the escarpment edge. Before you get to the drop-off, you will notice a smooth section of rock band on your right. You just need to get above this rock band. Keep your eyes peeled, there are numerous cairns all around this area, and they lead you up this same way. Once above the rock band, simply keep walking forward and to your left, you will find a footpath leading to the cave.
The drop-off is substantial. If you fall here, you will most likely be dead. It’s about a 90m vertical drop into smugglers pass. It’s mostly easy walking, but there is this one section about 5m or so from the cave that is the problematic bit for people who find the approach terrifying. If anyone in your group has a fear of heights, stay away from Rolands or rope up. I took my 13 year old daughter into Rolands last year and she was fine, but said that it was the scariest thing she had ever done (I’ve been taking my kids to the berg since they were 5 years old - she’s done Xeni pass and didn’t find that scary). My son, on the other hand, flatly refused to get into Rolands. When he saw the footpath leading what looked like into thin air, he sat down and refused to move. So we had to climb another 50m up to the rightmost upper Ndumeni cave.
So, you have options, see what works best for you. However, don’t underestimate the amount of effort required to get to Rolands in a day. Especially if you carry a heavy backpack and even more so if it is hot. If it is dry then you will need to carry additional water up as the top of Ribbon falls or the stream just before Mushroom rock is typically the only reliable water source before you top out on the escarpment.