On The Other Hand

I waited until retirement until I made aliyah for many of the same reasons you mentioned.  Since coming to Israel my main regret was not making aliyah earlier.
The life quality in Israel is different.  People seem to put value into the intangibles, both religious and secular feel the influence and benefits of living in a Jewish state.  Eighty percent of the women light Shabbat candles, an overwhelming have some type of Passover Seder. The overwhelming number keep some form of kashrut, since most of the slaughtering in Israel and the imported meat is kosher and one has to go out of his or her way to buy non kosher food (except for sea food).  The stores that carry Pork products serve the immigrants from the former Soviet Union who are not Jewish in many cases or have had no connection with Judaism for the seventy Years of Communism anti religion rule.
There is almost a universal feeling of brotherhod, even with a secular- religious divide that is exacerbated by political parties.  In time of war there is an almost universal desire by all to contribute to the war effort in some way.  Even Israeli expatriates in large numbers do everything in their power to return home and aid their brethren.
The average tourist expects to be entering a war zone when he comes to Israel and are amazed at the way Israelis go about their daily life routine about the same as most Americans do.  Frankly, when I come to the US in New York or Baltimore, I fear for my safety on the subways, buses and streets more than I do in Israel.  I walk home late at night without any fear, something I do not do in Baltimore or New York.  Children play freely in their neighborhoods in Israel with minimum supervision.  It is a great place to raise a family.  Language can be a problem for adults, but their are many Ulpans where one can learn the language much quicker than expected.  Children besides going to Ulpans quickly pick up Hebrew from ther friends.  Elderly people have more difficulty with learning Hebrew, but it generally is not a problem.  English is spoken almost everywhere
in most cities and with very little effort one can make understood by pointing to an item or in grocery stores and supermarkets cans, packages, and boxes     have labels in Hebrew and English and almost all have easily identified pictures of prodocts. 
Their are neighborhood community centers that have programs for all ages and where language is not a problem. 
I urge you not to have the mind thought of the spies that Moses sent to spy out the land.  They all agreed that the land presented many wonderful opportunities but ten of them reported it was too dangerous and difficult to live there.  Joshua and Caleb reported back that it was a very, very good land.  I stand with Joshua and Caleb.  Come live in this very, very good land!!

My own 8 year old daughter, also a day sch student, has not yet asked me that question—but I’m sure she will during our extended family vacation in Israel this summer!  Truth be told, I ask that question myself.  Family and finances. Yup, I hear ya, and lack of fluency in the language, sending chilren into the IDF, blah, blah, blah. But Friday night dinner with the grandparents as the deciding factor to stay here? I’m not sure that is the real anchor that keeps you here in good ole Pikesville—there are so many, many ways grandkids and grandparents maintain meaningful relationships in an era when most families are separated by great distances. Retired grandparents can spend extended periods of time visiting their grandchildren or even purchase a second home in Israel(after selling the Ocean City condo or foregoing the house in Boca). Actually, sometimes separation means that time together becomes that much sweeter and more consequential. Face it, if we “needed” to go to Israel b/c of some wierd American political, societal meltdown, we’d be on the first flight to Ben Gurion and never look back.(Just take a look at recent aliyah from France) There will always be a “good enough” reason for staying put b/c life here IS good enough. When I am most honest with myself I acknowledge the fear of the unknown and desire for stability which grips us all in middle age. the way I have come to see it, it is for us to encourage and support the life goals of our children, which will likely include making aliyah.  To stand in THEIR way b/c of Friday night dinner—well, then THAT would be the real betrayal and ultimate hypocrisy.