well, as a redhead :) - we are a difficult bunch. But i read that you're not much of a disciplinarian, but you need to be. Kids like us actually WANT structure. He is pushing the limits to see where he needs to stop. He probably feels out of control because he doesn't know where the boundaries are. If you think about it, not knowing boundaries is scary - you don't know where danger is, you don't know where trouble will start, you don't know when things will change. If you give a kid structure, they KNOW where to stop before danger comes.
He seems like he's running around and having fun, but he's actually thinking "Ok, what do i have to do to get a rise out of her. How far can i go before mom really notices me" So breaking a dish or something is his way of getting your attention "mom, if I do this, is that far enough for me to push?" so if you stop him and give him a strong signal that breaking things is too far, then he will think "Ok, so i know that i can go so far as breakingthings, but that's where it stops." otherwise, he'll keep looking for that one step further.
If you wait too long, he won't understand why you're all of a suddent punishing him for things he's been doing all along.
Punishment doesn't necessarily mean spanking, if that's what you have a aversion to. We "pop" once on the leg with our almost three year old. We only use that for blatant disrespect or something dangerous so that he knows, if we pop him, he better not EVER do that again. If it's a minor infraction (throwing a toy, not taking care of things, running in the house, etc) something that is not disrespectful to us or dangerous, he gets the time out or the toy taken away for the rest of the day.
Different kids need different punishments, but it's all about giving him a sense of what is safe and OK. Boundaries aren't restrictions or punishments, they create a "Safe place". It's like the railing on a cliff. within that railing, we feel like it's ok to walk around and look at what we want to look at and do what we want to do, but if we go beyond that railing, we're definately going to regret it :)
Good luck --- sorry for the novel :)