Sparkster, you are closest to how I am looking at events as well. Yes, Ben appears to be early-mid 20s. Jordan to be very late 20s-early 30s.
I can remember when Nicole was being used by her dad, who beat up mom, and Brandon interfered, getting beat up himself in the process.
And with Clyde being so creepy, I am thinking he may have molested/sexually abused Jordan, perhaps Ben tried to protect her, got beat up in the process. Maybe Clyde was a drunk, and abused them both. Jordan had enough, and wanted to protect Ben, and thus, took off, taking money to help them get started.
Is odd that now Clyde seems to want that money back.