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Also, as you fish, you'll eventually get fishing potions and better baits. Use the best rod and bait you have, and if you know for a fact that you're in the right spot... but are still having problems, use a potion. The higher your fishing level is, the better chances you have of catching quest fish, or higher tier crates.
Good Luck, and hope this helped.
He just tells you what kind of fish he's looking for that day (from 4:30 to 4:30), and if the day runs out while you're fishing, he'll switch to another fish. Only the quest fish he's looking for on that particular day can be caught that day, all other types simply aren't available.