Babies usually go home between 8-12 weeks old, depending on when they are weaned. And most breeders will want the baby to be maintaining weight for at least a week on their own before letting them go to a new home. I got my cockatiel at 10 weeks old. Usually most of their pin feathers are gone by 6-7 weeks. (I believe the bulk of pins happen around 4 weeks old). I'm not a breeder, but have heard from breeder friends that sometimes the parents or other birds will pluck the babies' feathers, forcing them to regrow new feathers (hence new pins).
Either way, your photos do show he has a lot of pins so I would just start by scritching his face along the grain of his feathers. Going against the grain now would probably be uncomfortable. You can also try gently pinching some and rolling them between your thumb/index finger to see if they are ready to break apart. Key through all of this is be as gentle as possible. He will squawk if you are too rough. And that may not mean he wants you to stop, it just means you need to be more gentle. Sometimes I accidentally pinch a pin on my Tiel, he yells, but he immediately bows his head again for more scritches.
You can also definitely go into his crest, too. My cockatiel loves it when I gently preen his crest feathers and scritch the top of his head.