I have an idea for making coated popcorn with caramel or marshmallow. I have not tried this yet. I do know popcorn gets hard and tasteless quite easy. Is there a different technique I can do or add a preservative to the recipe that would not affect the taste?
Moisture; biggest enemy; you need to make sure popcorn is dry and cool before packing.
Use coconut oil; something in the oil seems to prevent popcorn from going stale.
Packaging; I like to use large glass jars for saving popcorn. Air tight is a must.
The popcorn's problem is effectively staling -- and a sufficient coating will help to prevent this problem. You may need to add the caramel at a low enough viscosity to get a good coating on the kernels. You can always give them a second coating, if necessary.
It's also worth nothing that many of the places that sell packaged pre-popped popcorn tend to use 'mushroom' style popcorn. I assume it's so that there's less breakage of the popcorn during transport, but it's also possible that there are other reasons (eg, slower staling due to reduced surface to air ratio).