its easier, ill put 10 crickets in cup in the morning and it will help me know how many he ate and if i should put more in where free range i would have to look to see how many crickets are left and if any are hiding..... but free range gives your chameleon exercise by hunting food
I cup feed the majority and let one or two loose so Rebel can still hunt. It doesn't take long for him to hunt down two crickets and then he finishes off the ones in his feeding cup.. This allows for him to hunt and for me to make sure he is eating...
I do both, depending on what I'm feeding. I'll let crickets run loose but put roaches and worms in a cup so they don't escape. That way they get the best of both worlds but I don't have to worry about the roaches hiding in the plant pots for weeks or months. The crickets I don't worry about being loose, personally, because if I feed early in the morning it's highly unlikely that any will be left by the time night hits. And if any are left, one or two aren't going to be a big threat/danger to a healthy animal.
If you are worried about "exercise" you can always move the cup/container around, use more than one in the cage at different heights, and use a container that is large enough for the crickets to roam around in just like they would if uncontained.
I prefer to use a combo. I cup /bowl feed most roaches. termites and crickets. But I "free range" offer silkworms, superworms, indian walking sticks and butterworms because they cling well to branches/vines and are eaten quickly. And of course I free range moths. Grasshoppers I usually free-range too, knowing they will be hunted down immediately so no fear of them staying loose for long.