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Stout Mines needs to be done before Dragonspire to get the Dragon Armor; otherwise, you can't proceed far into Dragonspire (unless you get very lucky; I think Slug made it through without it ...?) But that's probably a fluke.
Boogre caves are strictly optional, but they provide a lot of great armor, weapons, plus advancing the Guild quests. Make sure you get your firepower up before going in there, though, because of the Lilies...
-Sazerac
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