John, it's really personal preference on how you plant you pots. If you want quick results, like the full pots you're describing, by all means load them up right away!
I actually do both. If I'm out of space in the ground to plant and just need a place to put them, I put fewer in a pot so I don't have to move them so quickly. But if I'm potting up extras just to make pretty containers then I'll put more in right away. The container you've pictured here will be filled in and beautiful in no time!
I very seldom water my hypertufa planters. Only in super warm weather. Otherwise I just let nature water them with rain. There's really not much grooming to be done with sempervivum if you top dress the containers like you did. That keeps weeds out and moisture in.
I planted a smallish strawberry pot (maybe 20" tall?) with semps a few weeks ago. I was waiting for it to fill in a bit before I took pictures.
Nice texture on the top edge of your pot. Did you do that with a wire brush?