I have news for you and can tell you that you didn´t break the quest:
1. Your quest has a unusual bug but i could find and fix it.
2. Instead of the squint deck, Richard is waiting for you in the tavern.
3. I could talk to him there but had to swim alone to Santa Lucia afterwards.
4. I had to change some stuff in your inventory to survive the crabfight (Elixir instead of little potions and Mixture added to Antidote) but didn´t take anything from your chest in the tavern. I took all needed things from chests of other ships and was only putting your little potions back to your chest.
5. After a very tough crabfight (because your health wasn´t good enough) Richard is appearing inside Santa Lucia automaticly.
6. I could play the whole quest without any further problems and the last save is infront the chest with all the gold for which you have only 2 days timelimit to bring it to your chest in the tavern.
7. I could also manage to restore your health completely after all, by using 2 bottles of Tears of Ixchel from other chests.
8. You can try to repeat everything that i did for you already and if you don´t succeed, you can use my save if you want.
9. I had to split the save folder to parts because the upload of filesizes is limited here. I have saved all my important single steps for you, so that you can repeat them if you want.
10. I can´t tell you were you met Richard because that is random (most of the times onboard of the ship Gloria, where the church is).
BTW:
Your Monster reputation is one of the main reasons why i don´t play the Jolly Roger DLC. Must be a hell of a job to ever recover from that.
Did you know that the Caleuche DLC will be startet by a random lighthouse caretaker in Guadeloupe, Santiago or Cartagena?
It looks like you didn´t finish the Final Lesson DLC in Saint Pierre which is limited to level 14.
You also missed a very lucrative quest called A Chief of Redskins which starts at level 8 in a random city, like Falce Trace which you could catch. You receive thousends of pearls from the indians which is very helpful in the early beginning of the game.
Have a nice day