Saddest naruto moment was Jiraiya's death, but in the new series, hearing boruto say his father doesnt deserve his food delivered and seeing that hinata made it, madem e think naruto's family isnt the happiest with him always being away.
Kind of makes me think of typical heroes, great at saving people, but terrible at saving them selves and caring for the ones close to them. (i relate it to some people in my family too that are quick to give out, than give in to the family).