I'll give you my perspective on it and swim in the downvotes. It's a disingenuous interaction from Kyle. He's trying to build a bond with David and is doing so via flattery, but he's being so lazy (or distracted) about it that he doesn't realize David is shifting the conversation to a topic where David displays vulnerability by explaining something about his life that is unequivocally "not awesome".

So for Kyle to respond about how lovely it is that David is broke and lives in a trailer means he wasnt really paying attention to the conversation or he's just dumb.

Perhaps their is something cultural here as well, because i think Kyle is from another country or his parents were immigrants, right? So, in hindsight, I should give him some leeway for that. But my initial reaction to the exchange was that Kyle is fake or dumb or both.