I'm happy to report that Winston's latest developments are not a fluke, they're continuing! Tonight he flew to me many times for treats - he even tried to land on my head twice just for kicks (no treat involved) but he hasn't mastered that yet. He just buzzes me and another time he almost landed on my glasses

He's still stepping up for both me and Dave - one time I offered to carry him over to the food dish during dinner, I offered my arm, and he very politely gave me a gentle peck with his beak to say No Thanks. I withdrew my hand, offered the food dish, and he hopped right up. We communicate like that beautifully with each other.
He's starting to relax when he's perching on us, but he's still on edge for the most part. I try to play the blinking game while he's on my finger/arm but usually his eyes are pretty wide and he's still too jumpy to relax that much. But tonight I got some good fluffs and some slight beak grinding while he was hanging out on me.
He really loves the forgaging basket too, he played and rummaged in there quite bit this evening - he's taking a liking to the balsa wood and sisal rope, he's getting new toys with those this weekend!