It’ very very hard- BOTH WAYS! From E”Y to America and from America to E”Y.
To completely uproot a child from what they are used to, and put them in a totally different foreign situation…
Not just materialistically, also Hashkafically.
As mentioned before, a child who their whole life wearing black socks- and see’s everyone wearing them, Rebbitzen’s, teachers… and then come to a charadi school and is told it’s assur without really understanding (it’s really pretty hard to…) is not really, legitimately CONFUSED.
and this applies to many other area’s also.
the opposite way- I just received a phone call about a girl who had just come from E”Y, where everyone her age wore long sleeves, and is utterly confused- her family, home, and other friends from E”Y all wear long sleeves, and here everyone in her class is not, and understandably, she’s very out of place.
One of a Yid’s lifelong dreams should be to live in Eretz Yisroel. We are only living in chutz laaretz today because of one of a few heterim.
The love for Eretz Yisroel should be ingrained in a child, just like a love for Torah and Mitzvos.
But if you are currently NOT living there, defiantly a shielah should be asked.