Caleb sure looks like he's in great shape to me. Cats especially indoor cats, really don't need to be fed as much as people think. I seem to recall that to maintain their weight, they only need about 300 calories a day. I do know that high energy cats like Abys will need more calories though.
I used to free feed mine but now I can't because Sky and Cirrus will eat everything in sight. I now feed them 2 times a day and they get about 1/2-3/4 cup of dry food a day. Storm and Sunny also get some wet food mixed in with their dry food. So far they've been maintaining their weights and Cirrus has slimmed down too.