Used to be pretty firm on this, like jokes about groups should basically never happen unless you're in the group. Then my buddy who's deaf did a whole bit about his hearing aids at a party and I nearly fell over laughing, and he loved that we laughed. Made me realize the person living it gets to decide what's funny about their own life, and taking that away from them is its own kind of disrespect. So no, laughing at your brother's joke about his own deal isn't the same as some outsider making that joke, not even close. The guilt probably just means you care, which is fine, but your brother handed you the laugh, so take it.

A crack across the windshield that nobody would own up to? That would have sent me through the roof. And dropping it at a Walmart parking lot in Cicero when you paid for delivery to your address is just wild. Two days late on top of all that, I can only imagine the phone calls you made trying to sort it out. The $1,150 versus $1,600 gap sounds small next to a windshield and a headache like that. For the record, cheaper brokers often just resell your job to whoever bids lowest, which is how you end up with a driver who does not care.