What about Rip Van Winkle's personality would have made him contented if he hadn't had a family? 

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mperez-mugg21 eNotes educator| Certified Educator

According to the narrator, Rip Van Winkle would have been happy without a family because he was the sort of happy-go-lucky individual who made the best of everything in life. However, even someone as easy-going as Rip Van Winkle couldn't be happy living with a quarrelsome and negative spouse. According to the narrator:

If left to himself, he would have whistled life away in perfect contentment; but his wife kept continually dinning in his ears about his idleness, his carelessness, and the ruin he was bringing on his family.

This interpretation of Rip Van Winkle's relationship with his wife is further reinforced by his reaction at the end of the story when he learns that his wife has died. Pretty much all of the changes that Rip Van Winkle encounters seem to cause him great consternation, except his wife's passing. In fact, when he learns that his wife has passed away he seems to be visibly relieved by the news.  This in turn suggests that Rip Van Winkle's easygoing nature would have left him content but the additional social pressures added on by his family in particular prevented him from experiencing satisfaction in his life.