寝太郎{ねたろう}はのんきに空{そら}をながめては暮{く}らしておりました。
My translation: Netarou was living by heedlessly looking the sky.
What does ては mean in this sentence?
Answer
「Verb A in て/で-form + は + Verb B」
means:
"to do A and B repeatedly as in a pair"
So, your translation looks good.
By far the most common and "famous" phrase using this structure would be 「食{く}っちゃ寝{ね}」, which is the colloquial pronunciation of 「食っては寝(て or る)」. That means "someone just eats and sleeps all day".
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