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They are always given by quests. The one who came from the tavern or from surrendering captain can always become captain.
If you want to get a proper officer, you have to save scum in front of a tavern, and reload until an officer you want spawn.
Loyal character will, but not often. And you can still offer them money so they stay. ( last option, then first option in the dialogue)
It is possible to recruit an officer if you are lucky with the tavern during the tutorial. As said above, just save before going to the tavern and reload till a recruitable officer shows there, helps if it is a new day and you havent visited tavern yet.
In general guys on floating raft have a lot of abilities already compared to those you can recruit on land. Saving/reloading on world map just before the encounter with the raft makes the captain different each time so you can try to get a great captain with many abilities (saving/reloading during the encounter wont spawn a different captain)