As for the Endurance question, I'll soon reach 70 in that stat and will see how much it'll effect my HP gain per level. I'm currently gaining 7 HP/level with my Endurance of 67, and I would guess I'll gain an additional one at 70.
When it comes to the shield question I found this; the armor skill of your shield type don't seem to increase when you successfully block. I was certain that it would but perhaps they've changed it in some patch.
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Nothing is impossible, it's just a matter of probability.
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