Leib K., Yerushalayim
My parents had lived in Eretz Yisroel for a short time after they got married. They bought an apartment in the Matersdorf neighborhood of Yerushalayim as they apparently intended to stay here long-term. They went back to the U.S. to be with my grandparents for Yom Tov and ended up staying in America. My mother always told me, "This was the biggest mistake that I ever made."
I grew up in Lakewood, New Jersey. As a child, I frequently heard my mother asking my father, "Can we move to Eretz Yisroel?" My father would respond that we could only realistically make such a move after the youngest child graduates from high school to avoid chinuch issues such a move would involve.
I came to Eretz Yisroel for summer vacation after tenth grade and stayed by my married sibling who was living in Yerushalayim. I traveled around the country touring and sightseeing. This was beneficial to me when I came back a year later for yeshiva—I was not distracted from my learning unlike many others to whom the country was new and exciting.
As a bochur, I had once heard a shiur by Rav Asher Zelig Rubinstein, zatza"l, in which he mentioned a statement made by the Chofetz Chaim about Eretz Yisroel being the safest place in the world. This had a profound impact on me and is part of what made me comfortable with living here.
Several years later, when I was a chosson, a family in the Sorotzkin neighborhood hosted me for the night of Shemini Atzeres. My host asked me if I was keeping one or two days of Yom Tov. I didn't know what to answer as I hadn't thought about it. My host mentioned that one of the biggest poskim, HaRav Yisroel Belsky, zatza"l, was staying by one of his children just downstairs and I could ask him for a p’sak. I found him sitting and learning in the sukkah. I told him that my kallah and I were planning to start out in Eretz Yisroel, but with no commitment for the future. I also mentioned that we did indeed want to live here as long as possible. He said that if my kallah would agree to me accepting a shteller (paid rabbinic position) here in Eretz Yisroel, then I should keep one day. I had no idea and no way of finding out, as my kallah was in America and it was Yom Tov, but when I did have a chance to ask afterwards, she gave a positive response.
After getting married in the U.S., we came to Eretz Yisroel a short while before Pesach. Since we had just arrived, we stayed in Eretz Yisroel for Pesach. In retrospect, I wouldn't advise newly married couples to make their own Pesach away from family. Life continued and it began to get difficult from a financial standpoint. After Pesach we rethought the issue of settling in Eretz Yisroel. We believed it really wasn't financially possible for us to stay here long-term. We asked HaRav Belsky, through a cousin who was learning in Torah Vo'daas at the time, if this would mean we should revert to keeping two days of Yom Tov. He answered in the affirmative, and that's what we did for the following Yomim Tovim.
I think it is very hard for young couples to live here if the wife does not have a job. There is also a psychological difficulty for women who can earn dollars back in the U.S. and instead work here at a job that pays that same number—only in shekels! Though the alternative of staying at home is worse because it leads to homesickness, which is a sure way to get right back on the plane. I know of someone who came here as a newlywed without his wife having a job, and to make matters worse, he stayed in yeshiva during lunch break. Although he really wanted to stay, they didn't last here too long.
The following Pesach we went back to the U.S. for Yom Tov. After coming back to Eretz Yisroel, we realized that we were much happier being in Eretz Yisroel. We felt that the level of simplicity and ruchniyus here really suited us more. After asking another shaylah, we were back to keeping one day of Yom Tov.
We first lived in Yerushalayim's Romeima neighborhood, but I was looking for a neighborhood where there was a shul in which the rav would give the derashos in English. We now rent in an area where there are several such shuls nearby (Ramat Eshkol, Sanhedriya and Sanhedriya Murchevet). Though financial struggles are definitely not exclusive to avreichim in Eretz Yisroel—and I don't think that finances here must entail being somech al haness any more than in chutz la'Aretz—I feel that at least here in Eretz Yisroel we have a big consolation that while we are emptying out our pockets and paying our rent, we have the added value of paying for our fulfillment of the mitzvah of yishuv Eretz Yisroel.
When my youngest sibling graduated from high school, my father was in extremely poor health. We did our research and found that all the advanced medical equipment and services he required were also available in Eretz Yisroel. This enabled my parents to move here, and my father was zoche for the last ten months of his life to live here in Eretz Yisroel and to be buried here. Our parents' love for Eretz Yisroel definitely made an impression on us children, and most of my siblings now live here.
Children and Eretz Yisroel
My rebbi, R' Yosef Stern, zatza"l, once told me that if I have a choice, it is better to raise children here in Eretz Yisroel, since they will need a lot less gashmiyus compared to what is needed for an average family in chutz la'Aretz.
I once asked my mashgiach why there were certain neighborhoods with a lot of kids from an American background "off the derech." He said that in his opinion, in many instances, it was because the parents were bashing the same local chinuch system they were sending their children to. If you're going to move here, you have to back the system you are going to send your children to.
An acquaintance moved here with teenage children. Although they had a tough time adjusting, having mentors from Yedidim—an organization which deals with such issues—significantly eased the transition.