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Yes you would be able to do watcher's keep at that level. Just remember to keep all the special weapons and artifacts you find in there so Cespenar can upgrade them for you when you get to ToB.
No when you start ToB you can't go to any of the areas in SoA. The only exception is that you can access Watcher's keep in both SoA and ToB. So you won't keep your guildhouse.
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