How do you get the animal portraits?

giving them the "best" version of what they ask for seems to help, too. If they ask for a fish, give them the most valuable one you catch. If they ask for fruit, give them perfect foreign fruit. (Or at least foreign fruit). And so on.

Perfect foreign fruit is how I've gotten both of the pictures I have so far.
 
Do whatever they ask you. If they want you to wear crappy clothes, wear their crappy clothes. If they want a horned hercules, give them the horned hercules you were going to sell at Re-Tail. If they want a tarantula (oh, you, Coach), take the risk and almost die while catching it. Send lots of letters to them and become best friends.
 
If you successfully unmask Blanca on April Fool's Day, the villager gives you their picture. I got Flurry's, Harry's, Portia's and Anchovy's pictures from it today.

- - - Post Merge - - -

If you successfully unmask Blanca on April Fool's Day, the villager gives you their picture. I got Flurry's, Harry's, Portia's and Anchovy's pictures from it today.
 
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