I love that the family actually needs money for once and that they're not millionaires. I like that they show them actually doing something about it (like getting financial advice) first, before Mr. Burns steps in. Chief Wiggum's speech about "retirony" is classic. Lindsey Naegle has some clever dialogue. Homer just throwing business cards at people is a good visual laugh. The Smithers musical is inspired.
I love Mr. Burns telling the vending machine not to wrap the toffee too tightly (because he's hungry now!). Love the pudding scene, from start to finish. It's a bit mean spirited, but it's silly enough to not be over the top (yet). The Comic Book Guy prank works in this way as well, also partially because CBG isn't a "nice" character anyway.
I feel like the episode would've been just fine if they would have gone as far as "Baby made a boom boom" and no farther. That's genuinely humiliating enough for them to make a point about Homer's dignity, so the panda rape is just icing on the cake that's not needed. And the less said about the fish guts, the better.