my headcanon for caboose is that he has very unruly hair that just GROWS and he likes it over his eyes. but sometimes when it gets too long and starts going into his mouth he has to get agent washington to cut it for him (no one trusts him with scissors for good reason). it used to be church because tucker refuses to (”oh my god caboose you can cut your own damn hair!”). when caboose finally took off his helmet after sidewinder(he rarely does) his hair just exploded out and was practically to his chin because it had been such a long time since it had been cut.
to this day no one is really quite sure how he sees out of it.
Hey here’s my hc on how Jeremy and Michael met: So in The Play we hear Michael say “say you appreciate that she’s smart”. So I think that when they were younger Jer got a good score on a kind of hard assignment and Michael was so amazed!!! So he just went up to Jer and started gushing about how he did well on the assignment and they were best friends ever since!