Reminds me of my uncle's poker night. Same six guys for like 15 years, then one dude brought up the school board and you could hear a pin drop. They went right back to arguing about who forgot the ice. I guess some groups just have one lane and that's it. Maybe try easing into it with something small, like a joke about potholes, and see who bites. If nobody does, you got your answer without the awkward silence.

Been running a milk crate for 6 years now, the black ones from behind the Kroger on 5th, they last forever. One thing nobody tells you, zip tie a small board across the bottom half so your screwdrivers and pliers don't slide out the side holes. Also cut a piece of old inner tube and staple it around the top rim, saves your hands when you're carrying it loaded up stairs. Buckets still win for wet stuff though, I keep one just for muddy boots and rags. Crate for tools, bucket for junk, that's the setup.