I was thinking exactly the same thing, I was even contemplating putting an IP camera in there so I can check up on my baby when away.
Thinking about this more though, I am an electronics engineer/programmer who dabbles in android too, I wonder if an old android phone could be converted, or maybe a bluetooth feeder, connect it to an old phone, text it, boom, locust come out.
To be honest, the only way to make this work would be something like a container with say 7 compartments, two insects in each, then each feeding time, open a compartment.
I need to sort something by august as we are away for a week, I think some prototyping is in order.
Everytime I go away for work or vacation I have to bother my brother or friend to take care of Dexter. They don't mind doing it, but I know it's a hassle. And I always have to wash my sheets and lysol my couch when I come back. Hehe.
Just 'free range' your enclosure with crickets and leave food for them at the bottom of the cage, so they have something to nibble on besides your cham at night.
I've taken several trips for two weeks at a time, when i had my Veiled, and when i got back he was fine. Veiled's unlike other Chams can go quite a long time without water( they can get their moisture from crickets and fruits/veggies). Just make sure he's VERY well hydrated before you leave.
If your vacation is 3-7 days, he'll be OK without food. Just feed him well before the vacation and he'll be just fine without any food for a week. And while gone, you could leave some crickets running around in the cage for him to snack on. Don't leave too many, maybe 15. You don't want them bothering him in the middle of the night.
If it is a young chameleon, then you need to find someone who can feed him... if it's an adult (12+ months) no need he'll be fine.
You will need an automatic watering system like the AquaZamp though