I'm pretty sure that "replace the homeless man with a park bench" image was a reference to some TV show making a gentrification joke, but I can't put my finger on it. Anyone recall?

Yeah, I couldn't help myself on that one! It's a reference to the Cypress Creek promotional video from the Simpsons.

https://www.youtube.com/watch?v=foU9W7AkKSY

Simpsons, the Frank Scorpio episode. The advertisement for the company town shows a beggar slowly fading out and being replaced by a mailbox.