gavra: Can I recommend “Out of the Whirlwind” by Rav Yosef Dov Soloveitchik? While it is primarily a book about hashkafa after the Holocaust, it also deals with some of the issues involved. He also gave a shiur on the specific considerations a ben Torah should weigh when considering aliyah which is printed elsewhere.
I can’t say anything about aliyah, since I haven’t yet but I really want to.