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Equip the 'Can-Do' perk if you have it. Even just one point will get you tons of canned goods, including dog food. It can trigger at almost any loot container you mouse over.
if you HAVE the goods handy, good do it
otherwise its better to just get the repeatable exp one
* 100 pre-war money (the challenge to collect 100 of this used to show up often, but doesn't seem that way anymore).
* 10-25 pre-war food (canned dog food, cram, blamco, fancy lads, etc.)
* 10-25 nuka-cola.
* 10 alcohol, including a few vintage ones.
* 5-10 weapons that need repair (most enemies' guns have good conditions that don't need repair, a most obvious but least remembered fact; if you get a challenge to repair guns and don't have them, good luck; Bethesda did this on purpose, of course.)
* 5-10 armor that need repair.
* A few costumes, for costume-related challenges.
Check every trash can in the Whitespring Mall. (don't bother with Whitespring Refuge).
Check every trash can outside the Whitespring. Check the Trashcans in the Whitespring Club House, and around the pool there.