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The reality is, the Angler simply has a "Fish of the Day", which is only available that day. If you "take the quest" at 4:31 AM, you have 23 minutes and 59 seconds to complete it, and if you "take the quest" at 4:25 AM, you have exactly 4 seconds to complete it. Then he'll want another fish and the previous one becomes uncatchable.
Also, you should use Sonar potions while fishing to save bait. No need to catch every Bass and Princess Fish and whatever other crap bites, you can just wait until something you want bites and then reel it in. You only lose bait when you try to reel in something.
If I remember correctly, fishing for a hallowed underground fish in a converted tundra won't work, it needs to be a purity converted to hallow. However, you can get the shrimpy truffle from the converted tundra.
Also, look at the background so that it matches the biome you need. If a quest only says "surface" "underground" or "cavern" then you actually needs to be in a purity for them to show up, it can't be a corrupted surface, or a hallowed underground or a mushroom cavern.
Also note that the time frame for the fishing quest is when the new day begins and not when night starts.