As with all important steps in life, it is very wise to consult a gadol. A gadol I know has told certain families to go to Eretz Yisroel and others to stay put.
Eretz Yisroel is not just another real estate location, as you know. One who lives there is in the palace of the King of Kings. There are those that are going to grow spiritually there and flourish, but others will find insurmountable issues, and may have to return to Chutz La’aretz.
One thing is certain, Hashem guides us and lets us know where we can best serve Him. If the idea of aliyah is coming up over and over, then that may be a sign to begin the process. For some Jews, that idea NEVER crosses their mind as a viable option. It is not fair to judge anyone’s choice, or to say lashon hora about Eretz Yisroel. If Hashem wants you in His most beloved place, mentioned ???? times in Tanach, He will help you arrive and stay put. A few unique to EY yissurim will probably be thrown in to give your neshama a challenge, but it will only be given to because you are meant to accelerate to a faster level of soul refinement in the palace of the King. People in CHUTZ Laaretz have plenty of yissurim, too. Just take a look at all the news-there is no trouble-less carefree place left!
And btw, you might be surprised to know that quite a few American charities solicit in EY on behalf of Jews needing help in the USA.