1 : Yes, when Bolt is cast targetting Nadu, Nadu's ability triggers, then when you activate and resolve Spellskite's ability, the Spellskite does become the target of a spell and so the ability granted by Nadu to the Spellskite triggers too
2 : You can activate Spellskite's ability multiple times but since it's already the target of the bolt after the first instance of the activated ability resolves, the target does not change, it does not become the target of the spell, so the triggered ability from Nadu won't trigger any additional times.
If you had multiple Spellskites, you could change the target of the Bolt back and forth and trigger their respective triggered ability granted by Nadu, but note that this ability has a restriction of triggering only twice each turn (for each creature, since they all have the ability)
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