This is a very interesting and touching story, Gabe. Interesting to me, especially, because we are at very different points on the age spectrum--I was 68 when I decided to move to France. My experiences are viewed through the eyes of a much older person.
Yet, I agree with much of what your write--homesickness, loneliness, missing out on family events, all are part of the price you pay for choosing to live abroad. I've also paid the price.
Despite all that though, it has been and continues to be an incredible experience. I've never regretted making the decision. I hope you find happiness and contentment wherever you live. My best wishes.