@RyanBRZ I've always free-range fed at least half the feeders I'm giving my cham, but I make sure to be selective like everyone has described. In other words, I'll easily let crickets free-range in the cage and my cham loves to hunt them! I have a feeder cup very similar to yours and that's where I make sure to put all the other feeders (roaches, worms, etc.) because they hang out at the bottom, fall to the bottom, etc. and then my cham ignores them or they fall through my drainage holes. My crickets will sometimes get through my drainage holes (rare), but they fall to their death into the drainage water and drown, so it's really just a small waste of money to me, but like I said, it's rare for my setup.
Based on my experience in "dumping" crickets in a free-range way, you're going to get the calcium powder (and other supplement powders) all over your enclosure if you don't think about it first. I learned this the hard way and ended up cleaning up a big mess, haha. I use a mason jar for dusting my crickets (a lot of people use a bag or an old peanut butter jar or something idk), and first I just make sure there isn't a huge amount of the supplements in the jar, put my feeders in, shake it around a little, and I'll tilt the jar horizontal in the enclosure and allow the crickets to crawl out and onto the vines and branches naturally. This avoids spilling the powder everywhere AND the other feeders (worms, roaches, etc.) tend to not be as active and ready to crawl out, so they're usually last and I shake them out last into that DIY feeder cup which will catch any of the powder that escapes my jar. Every 2 weeks or so I clean out the feeder cup really well with an old toothbrush and a diluted vinegar solution because it gets grimy. Eventually I'll probably need to start fresh and make a new one, but honestly it's held up really well with me just keeping it clean.
When mine was 3-4 months old he would eat 18-20 small crickets in 5 minutes. It blew my mind away and I thought I might be over-feeding my little guy, but looking back I wouldn't change the amount. I would have been better about the variety from the beginning, but you're already doing that! You don't have to worry about cutting back until he's about 7ishhhh months old, emphasis on the ish because I've read a lot of different opinions on the timing of this actually. The one common trend is that you want to gradually taper the amount you give them or they'll get grumpy (hell, I would too!). A very established member told me to cut back 2 crickets every 2 weeks until I got to a better number.
OH another pro-tip for the morning routine and lights. My lights are 7:30-7:30 but sometimes I have to wake up earlier than they turn on and I have to get ready in the dark (my setup is also in my bedroom). I use a headlamp or flashlights. I'll even plan my outfit the night before, or do whatever I need to in that room the night before, to spare my cham! Anyone watching me would think I'm nuts, but if you turn on over head lights or even just one lamp (even a low/dim lamp) it could wake your cham early and he won't be getting his rest. The reason I have the headlamp is for the feeding. Your cham does need the food for the first half of the day to properly digest. It's better to put all of his feeders in the feeder cup while he's still asleep and then you leave for the day, then to feed him too late in the day. I've done this on those days I have to leave super early in the morning. Hence the headlamp! That way I can work with my hands and prepare everything, open the enclosure, dump feeders in his cup, close it up, and know that my little guy wakes up with a pleasant surprise lol.
SORRY I KNOW TOO LONG. Nobody will believe me, but I try to be concise. It's all for the love of chameleons!