Welcome Kris.

It sounds like you have two different EDCs- one for when you are in town, and the one for when you are off the pavement? Or am I misreading that?

If I am reading it right, I would say that maybe you need a tiered or layered kit, where you have the stuff you have with you unless you are sleeping or in the shower, and then determine what you need from there, depending on your environment.

As for overkill... That's hard to do unless you start needing pack mules and/or local bearers.