I have a simular feeding regime to Marcia's clan.
Feed: good wet-2x per day
Free-feed: best affordable quality dry.
As a rule of thumb, I have always fed my kittens as much as they wanted, the first year. They are burning zillions of calories a day as growing kittens.
The second year, I slowly worked them into an adult daily routine. By 18 months mine all ate the same.
As Marcia said, some prefer schedule only feeding. (No free-feeding)
But the same would still apply as to the amount.
Earning trust from a cat is a long and lengthy process, sometimes. It really does depend a lot of what the cat has been exposed to. Just relax, take it slow, don't get frustrated, your kitty needs to take things slow. You are HUGE in his eyes and very unpredictable and possibly dangerous.
You're not alone, I've got a couple of scaredy cats, myself. I know it can be hugely frustrating as well as disappointing. You're not just a food supply to him, honest. He has a certain trust in you already. Cats will not hang around if they feel threatened or nothing is "working out" for them in their current situation.
Good luck with Oreo.
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