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While nothing in life is simple, things are often complicated by those that make it complicated. The difference between families that succeed and fail in aliyah has more to do with their attitude than their family/parnassah circumstances. People with a cynical attitude who are unable to be flexible will certainly have a hard time. People with difficult life circumstances and older children can succeed if the family has a positive attitude, and willingness to be flexible and roll with the punches.
There have been tremendous changes in the last 10-15 years. Bet Shemesh is a town that has more Jews than Monsey, and will be doubling its size in the next couple of years. Bet Shemesh has exactly the type of yeshivish that rational described. There are also many more affordable places that have an out of town vibe, but require more israeli integration.
Most children do learn the language and adapt. Average children below the 5th grade pick up the language in 3-6 months. The older children take longer, but eventually they pick it up. Most do NOT move back to the states. Since I moved to EY, perhaps less than 1% of the people I met expressed a sentiment that they would want to move back to the US. Amongst frum Americans, there is a very high satisfaction rate of those living here. That does not mean that it is a rose garden, but life satisfaction overall is very high.
There are several schools that offer limudei chol for high school, and they have dorms for families that live further away. Many people are happy with these schools. There are also a growing number of vocational training programs for chariedim, that do not require one to go to a high school with limudei chol. Specifically IT and computer related fields dont require formal high school education, pay very well, and have programs for chareidim.
While no one supports breaking up a family, you can go along way by creating a positive atmosphere in the home about aliyah. Shabbos stories about EY, music, pictures, food, and just talking about EY in a positive way can go a very long way in bringing other family members on board, gradually. It took me quite a while to get my wife on board, but now that weve lived here for a few years, she is happy here.
You are ultimately in control of your own happiness. You have the power to chose to be happy or not be happy. If you are a flexible person with a modest outlook, and you want to come to EY for the right reasons, there is no reason in the world why you cant succeed and be happy here, regardless of personal circumstances. Will everything be smooth and easy- absolutely not. But if you realize that EY is a tremendous gift, and you appreciate the gift, and you are willing to go with the punches, there is no greater joy than living here- even with all of the problems. Although American chareidim are still a small minority, they have built up enough yeshivos and mosdos for themselves and their children to be self sufficient. The more people that come, the more options that will open up.
Dont get discouraged by the 1% that moved back to the US and are bitter. Talk to the 99% of those that are living here and can tell you the facts from a positive perspective.
Good Luck!