Hey! I have a middle-aged, 17 year old cockatiel, Bobi, and we're very attached and thought I'd share my experiences, I have a few tricks, which were very valuable to me throughout the years.
I think that you and Freckles are starting off really well, maybe you are trying to handle him too much too early. Birds are very curious, so they'll take interest even if you keep your distance a little. I have a little story here: Originally Bobi was bought to my bigger sister, but he became more attached to me, and ended up with me. The difference was how we handled him. My sister used force more often, and I used to play more often. It's a good rule to leave birds wings and tails alone. They can be made to tolerate it, but they won't like you for it, after all, your messing up the feathers they work all day to get all neat and beautiful. Putting your hand over his wings should be enough to keep him from flying away.
I suggest keep him company as much as you can, but take your time before you handle him, talk to him, whistle, try to arouse his interest, and only then make moves to handle him. Birds are very social, especially those who live this long, so they need contact from you. But first you have to be very interesting, so he knows he wants contact from you. Always handling him when you want it to isn't a good idea, even if he cooperates. Initial force handling is essential since you prove to your bird this way that you wont hurt it, but after he knows he won't be hurt, and Freckles knows that already, you want him to start to really like you, especially if you want him trained
Make lots of sounds
They love their feathers.
I have tons of stories with Bobi when he instantaneously got friendly with somebody who had a big pretty feather and played with him a little. And have some funny attack stories. A friend of mine kept touching his tail feathers. Bobi was very angry with him. One time my friend went to check out what was he doing, the cage door was open but Bobi was inside eating. My friend didn't do nothing, but stood there and watched, and Bobi came out and leaped staight at his face scratching and biting him. They never became friends
Bobi loves all kinds of pointy objects, like pencils and screws, they will make great play things. Feathers are the all time favorites, however. If he becomes more comfortable, try putting him on a big table with little play objects scattered, let him discover them. Don't force the toys on him. If you play with something and is interesting enough, your bird will join in by himself.
You can try little rubber or plastic balls too
If you have some new food to offer, try putting some on a clear surface of contrasting color, light color seeds on a black tabletop or paper, colorful bits on white or black, dark bits on white. I always succeeded this way to make my bird taste new things. I start to nibble on some, and then he can't resist, it looks so good.
I keep my bird loose now, even when I'm out of town, and the neighbor has to feed him. When I lived with my parents, I had to keep him shut most of the time. It was hard to catch him, and not because he wasn't social, he was already very attached. He just didn't like to sit in the cage all they. And when he was let outside, he did make a lot of mess all over the place. After I moved out, I didn't care about the mess, and started to keep him free. Guess what? After a little while he chose one or two favorite spots and that's that. No mess
He goes exploring from time to time, but most parts of the house aren't comfortable enough to stay there. So I started using this new insight as tricks. If I wanted to keep him in a certain spot of my home I made sure it's comfortable for him. Anyway his favorite spot will always be close to you. And now he sits on top of his cage most of the time. He sleeps and eats inside the cage, he goes in by himself. I only lock him up if there are lots of people coming and going, and he could get stressed and scared. I think keeping their bird loose is a goal every bird owner should work towards. I find life a lot easier. Less noise, no chasing at all (before we had hide and seek routines before going "home", Bobi always read my mind)
and there is no biting the neighbor when feeding, if I'm away.
As a little kid when I wanted to take him out of the cage, but didn't want him to fly around, I came up with an idea. I spread a bedding cover across the floor and made a little tent, half a meter high, and crawled in with my bird, and let him loose there. I was about 10 (now I'm 26), and it was really big back then from the inside. Light seeps right through, and there are no holes where the bird could escape. No chance of your bird getting hurt somewhere around the house, no chance for him to fly away, so I didn't need to keep him in my hands inside there. It was the perfect place for bonding. That's where my bird got into the habit of crawling all over me, and later the floor became our main playground. I'd sit on the ground, have a quill in my hand, and wherever I put it, Bobi would fly there, from one place on the ground on a part of my body, to another place on the ground. It's not that common for birds to become that comfortable with the ground, they like heights by their nature. So I suggest a tent!
And speaking of heights, if you want to pet your bird, scratch his head, make sure your hand is at a level below your bird's head, or at his feet. If your hand is above his head, it means threat. It makes birds more comfortable if they are the same "height" as you are, and you don't tower over them. Even if your holding him, keep him at your head level, they don't feel threatened that way.
This came out quite long I think, but I hope it will really help you to bond. Birds bond more easily with children. They are smaller, have higher voice.
Good luck!
