you know, i'm just thinking about that one conversation in episode 77 (just before jester wakes essek up in the middle of the night with a shit ton of sending spells), about whether or not to ask essek for a teleport to rexxentrum
and they have two arguments against this (neither of which are don't message essek at like 1am)
the first of which is "i don't think we can ask essek to just teleport right into enemy territory"
and the second of which, though it does start as caleb's reasonable concern about favors, quickly mutates into "we can't keep asking essek for rides everywhere like he's our older brother"
and knowing what we know now about essek, both of those are hilarious in retrospect