Always do the Dragonspire LAST -- for the simple reason that it's a hell of a long walk from Brimloch Roon to Ishad -- there are a ton of quests you need to farm near Ishad first. You want to get your guild levels up as high as possible so you can start getting the cooler skills.
The exit from the dragonspire maze comes out on the north side of the mountain -- to get back to the Ishad area you have to jump off the top of the ramp (or crawl down the side of the mountain), or else go back through the maze inside the spire. It's a pain.
Painbringer
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