If you think your plant is getting too big, pull off the pups. If you like it the way it is, put the whole plant in a bigger pot. No one is separating these plants out in the desert - you don't need to either. I personally like the big overcrowded plant look.
The best time to repot a cactus or succulent is in the spring just as they start to grow. Succulents can get pretty crowded before they need repotting. I love the look of yours and would leave it alone unless the pot is tipping over from the weight.
Out in the desert, there is constant competition for water and nutrients. The roots spread out just under the surface of the soil and the plant absorbs ever drop of water that comes its way.
(in fact, cactus and succulents have no shut off valves like other plants do. They think that they need every bit of moisture that comes their way). So, you are the goddess (or god) of the garden. Everything you give your cactus or succulent will be greedily used. So be stingy - hold back.
And, in that pot you have confined this plant with free ranging roots to, every drop matters. Under pot and watch the water.
Daisy