The second ending should automatically begin once she gets caught by any pirate. (how did you escape? convo) Once she gets about 60$ in her wallet she should continue and end the second ending. (need a place. convo)
Sorry, the 500$ mention is just idle talk about the price of things in the capital. It has no bearing in the actual gameplay. I'll remove it in the next update.
If you have not had either of those conversations I'll need to see your C:\Users\USERNAME\AppData\LocalLow\Delusria\Salvor DEEP\PlayerData.json