What would be the best decision for a person who earns a good living, their children are going to good schools and are very successful in learning Torah, but they have a very strong desire to move to Eretz Yisrael?
There are three primary opinions among the Rishonim that discuss the importance of living in Eretz Yisrael.
The Ramban holds that it is a biblical obligation to move to Eretz Yisrael and also to conquer it. He holds that this is the fourth commandment that Hashem promised to our forefathers, where He told us not to forsake the land to other nations and not to desolate it. This is also the opinion of the Rashbetz.
Baal Halachot Gedolot and others don’t mention this mitzvah when they list all the mitzvot of the Torah. It looks like they hold that living in Israel is a Rabbinical obligation. The way that they explain the verses that Nachmanides brought down is that it only applied to the first generation that went through the desert, but not to future generations.
The third approach is that of Rav Haim Hakohen brought in Tractate Ketubot which holds that today there is no mitzvah to live in Eretz Yisrael because there are a lot of commandments associated with living in Eretz Yisrael which cannot be fulfilled properly, and therefore it is better to stay out of Eretz Yisrael. However, it is important to mention that the Maharit (volume 2 siman 28) comments that this opinion is not actually from Rav Haim Hakohen but from a student that did not understand him properly. Nevertheless, Harav Kluger in his book Haelef Lecha Shelomo (siman 118) uses Rav Haim’s opinion to allow a person to remain in Chutz La’aretz even after making a vow to go to Eretz Yisrael if it is too difficult for him.
There are multiple interpretations as to what the Rambam’s opinion is. Some hold that he considers living in Eretz Yisrael a biblical obligation and the reason he didn’t include this commandment in his list of mitzvot is because it is a general mitzvah and not a specific mitzvah. Others explain that this mitzvah is already included in a different commandment where it says “Rather you shall utterly destroy them” (Deuteronomy 20:17). And others say that the Rambam holds that it is a Rabbinical obligation.
Rav Chaim Midini says that after discussing all the opinions above his conclusion is that if one has a good livelihood and is uncertain about his future livelihood in Eretz Yisrael then he should stay in Chutz La’aretz. Similarly, the Bet Halevi (volume 2 siman 3) says that if one will live in Eretz Yisrael but will be dependent on money coming from Chutz La’artz then one is not fulfilling the mitzvah of living in Eretz Yisrael.
Also, the book Teshurat Shai (volume 1 siman 28) says that once a person is working to feed his family, that can be considered a person who is engaged in one mitzvah and is exempt from another mitzvah.
Rav Moshe Feinstein (Igrot Moshe volume 1 siman 102) says that one is not obligated to move to Eretz Yisrael, but if one does, they are doing a mitzvah. However, moving out of Eretz Yisrael for no good reason is a sin, and he brings a proof from the Rambam who says that one can live anywhere in the world except for Egypt, however, if one moves out of Eretz Yisrael then it is like he has no G-d.
Without a doubt, it is a great mitzvah to move to and live in Eretz Yisrael, but at the same time one needs to be very cautious and careful to look at his financial status and his children’s education before he takes this giant step.