Thanks for your input. I certainly agree with #1 and it is definitely in our plans. I don't see any real benefit to not deballing him.
About #2, I do think he connects the dots. I was going to add this bit, but completely forgot. One of my favorite things about the dog is that I can tell when something bad is happening or has happened based on how he's acting. In short: If his ears are back or he's staring at me cautiously, something is amiss.
He does this pretty often and it's generally spot on. Today, for example, he jumped on the couch and put his face inches from my head with his ears back. I was doing work and not really paying attention to anything going on at the time. As I looked at him, he immediately looked away to the direction of his food bowl...where the cat was quietly and cautiously pilfering feed from the dog. He knows that I yell when the cat does this, so I think he was actually apologizing for the cat's behavior.
A little later today, he was asleep on the opposite end of the couch. He woke up suddenly, sat beside me, and put his ears back. I told him it was okay, nothing bad was happening...and then he started doing his pre-puke gagging. I put him outside, he puked, and everything was back normal. It was basically just him saying, "Umm...something fucked up is going on...help?" It pleases me.
Connecting this back to the trash: Whenever he's recently chewed something and I'm coming inside, he'll greet me at the door, oftentimes without barking, and he'll have the ears back. I'll immediately know he's done something and can normally tell where the mess is by simply going in the opposite direction of where he's going (if it's in a bathroom, he'll go into the living room looking back at me...if it's in the living room/kitchen, he'll hover in the hallway). This tells me that he definitely does know what is wrong...but that he either isn't able to control his impulses yet or he simply doesn't care to.
I'm inclined to think that he legitimately can't stay away from an open trash can if there's no supervision, though. I know that he can't control his barking sometimes. Maybe this is similar? For example, if he hears something outside that really gets him going, he'll go apeshit. He is a dog, after all. I'll normally calm him by calling him over and putting a hand on him. While I do this, he'll continue to bark, but he'll stifle the noise (into a bruff) and look at me sadly as he does it. It's like he knows that he shouldn't be barking, maybe even that he doesn't want to be barking, but they still eek on out.
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