I trained my cat to shake my hand. It's the coolest shit ever.

Anyway, it sounds to me like he's so used to being outside that he doesn't like being inside. Consider getting him a harness and taking him outside. I know it sounds stupid, but that's what we do for our cat and while he hated it at first, he now follows along like a dog would.

Also, try getting some perches or cleaning off the high points of your apartment. Most cats like to be up as high as possible, and restricting them from that can make them very uneasy/uncomfortable.