Money Maker

sounds like the girl was manipulating him by using him. he knew she didn't like him for him, but just couldn't let go of her. use plays with his emotions and the relationship never actually becomes anything.

Hey my my, she's gonna take ya Way down down, she is bound to break ya

"I want to buy some time but don't have a dime"

(...)

"Hey my my she's a money maker"

excelent.

"Oh, she just keeps me guessing Oh, never tells me yes and"

"Yes, and" is a term used in improvised acting - it involves accepting "offers" made by your scene partners, and expanding upon them in an interesting way.

For instance, your scene partner might say "I never thought you'd show yourself around here, Captain!", and you might reply with something that accepts and expands on either being an authority figure, or being unwelcome, like "This place has the cheapest zeppelin fuel."

The purpose of "Yes, and" in improv is to expand upon the scene and continue telling a story in a way that is true to the characters. It is the essence of supporting the scene and the people in it.

In improv, refusing an offer is known as "blocking an offer", or (colloquially), saying "No, but". It is refusing the input of your scene partner and putting your own ideas out in their place.

In the context of the song, "[She] never tells me 'yes and'" reads like an esoteric way of saying "She never supports me" or "She's always disagreeing with me".