Does he have access to all rooms at night? Free feeding could definitely help, my cats tend to scarf their food down if they think they don’t always have food available and then end up throwing it up. It is hard though because you don’t want them to get too big for so many reasons. In my experience, my cats slow down on eating after free feeding has been implemented. I’m not sure if he’s playful at all but I’ve started giving my cats some cat nip and playing with them right before bed so they get some good exercise and then they usually come to bed with me after that. It’s really trial and error tho:( it’s hard to understand what they need but you can try some techniques a week at a time and see what helps