I worked in radio and in the music biz (half a hundred years ago). So I used to know a tiny bit about this.
It’s not a financial decision, at least as the question is framed. Different songs do not bring different royalties.
What You Didn't Know About Terrestrial Radio Royalties
It is a financial decision in that the rates advertisers will be willing to pay are based on the numbers listening. (And also on who the advertisers are. So who advertises? Largely The Villages itself, so their preferences are likely taken into account.)
But my guess is they are mostly playing songs that will let the listener say, “Wow, there’s a great one I haven’t heard in a long time.” Beatles and Stones and the blockbusters still get played but perhaps down rotation and maybe songs that you don’t get on the other oldies stations. Call and ask the program director if you want his or her take. Or call and request what you want. If enough people do, they’ll play it.