A friend testifies that about twenty years ago Rabbi Chaim Zev Malinowitz zatzal brought his whole family on Chol Hamoed from Jerusalem to some northern Israeli religious settlement (including a yeshiva) he knew, a “shining settlement on a hill”. This he did by renting a bus (not a minivan) and filling it.
And it was a “real” settlement: off the beaten track, surrounded by hostiles, all hands carrying guns and doing guard duty shifts.
Rabbi Malinowitz, he says, was trying to endear the frontier and the special Jews who settle there to his oleh family, who grew up in a different environment, with different ideals.
And he couldn’t be happier doing it.