I think at 14 weeks he could be free fed. I have always done schedule feedings and my two thrive on it. I think at this point, if I left food out for them...they would stuff themselves. I'm actually trying to cut back a tiny bit to get about a half pound off both of my pups. They put on some winter weight, and because I schedule feed, I can control how much they are getting.
I don't use a measuring cup, but a shot glass for their food. They get a little less than a shot for breakfast and the same for dinner. They weigh in at 7.5 and 6.5 pounds respectively. They should be around 7 and 5.5-6 lbs... I'm sure with the increase in exercise, they will get there, along with mommy
Sorry for the tangent!