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If you pickpocket him, he will keep saying that he's still suspicious about you, even after checking your bag.

This will prompt some persuasion options that, if failed, will get you in a fight against the whole settlement.
that's same for many other characters. dunno what procs them though
If you progress to Act 2, he will be doing something at Paradise Downs. Do his quest first before you go to the Black Pit. If you go to black pit first and finished the story there, Gareth will go missing after you talk to him again. When you proceed to Act 3, malady's dialogue suggests you get him back on the ship before you go, but I heard people say he appears in Act 3 anyway.

Scyths

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This is true, I took his quest and did it on the way of finish the whole blackpits area, and once I came back to close the quest it closed but Gareth walked off and I didn't see him anywhere yet Malady kept telling me he was missing ...
Spoilers ahead: The journal said Gareth left paradise downs after I went the mercy route with jonathan then killed the monks, Malady kept telling me that we're missing Gareth when trying to progress to the next act, in act 3 he appears when you go to meet Alexander and you need to pass a strength or memory check to have him stand down, otherwise you need to kill him.
yeah malady say we need gareth before leaving lady vengeance but i cant find him on paradise downs. he is missing and yeah, i killed the magister who killed his parents and have his vengeance but whatever..
sorry for the late respone but you will still find him in the next arc, i believe the only way to sail with him by your side is to have killed jonathan the first time you see him.