Of course, that's intended to be ironic. In a feat of self-envy, he is one of the poor people that he's talking about. But for a week or two out of each year, he puts his hard-earned savings to work and lives like a king. He knows that the next Monday he'll be back at the grind. But he's going to enjoy the luxuries of resort living while he can.
King Arthur felt the exact same trappings in the Broadway musical Camelot, but in reverse! Anxious over his pending arranged marriage to Guenevere, he paces the forest and hypothetically ponders "I wonder what the king is doing tonight". In his soliloquy, he assumes the role of the peasant who enviously gazes at the palace. Then he answers his own question:
He's numb! He shakes!
He quails! He quakes!
That's what the King is doing tonight!
The king — with all his riches — is actually longing to be a commoner, who obviously has no problems at all. And my friend wishes to be rich, so he could wonder what it's like to have all the problems of the poor people.
It's a paradox that defies reason: The grass is always greener — no matter which side of the fence you are on.