I went through doing those quests over and over again. Especially the Josie McReedy quests. But I had enough gold and it seemed like I wasn't really getting anything. Soooooo, I went on my own and leveled weapons. I've now started a new pirate, and working on questing with lil Rose
I did notice some of the quests dropping off the list, but I was always able for find something. With Josie, if she gives you something you're not up to doing, just back out of the menu a few steps and request again. Usually she'll offer something else. Sometimes I did that a few times before I found something I wanted to go after.