I think you're right that he'd be very happy to hear the "I swear." Though also wistful that he never got to hear it earlier.
You killt me dead here. I'm crying again. God, I remember more than a year ago someone asked on imdb when the tears will stop. A year has gone by since then, a whole year. But still.....
Yes, I also think Jack would have been very happy about Ennis's evolvement. Seeing Ennis with his parents would have meant a world to him.
I think Jack would want that Ennis continues to grow and to feel more comfortable with himself and his life and that he finds someone else. That's what you wish for when you love someone. And I think there's hope that the first part comes true, at least to a certain degree. But I don't think Ennis will ever find someone else for two, no three reasons: first, I think he won't get comfortable enough to be free for another relationship. Second I think Ennis is a one man man. He loves Jack period. And third, I think he won't live long enough to reach an age in which you kinda stand above ordidinary affairs, above rules that society puts on you (and there are many people who live really long without ever gaining this freedom and relaxed manner). I'm still with Jeff (Wrangler) on this: I think hard outdoor work, poor diet and health care, plus cigarettes and booze will put an early end to Ennis
.
But no, I don't see Ennis's future all in black. I hope that he will have grandchildren pretty soon and will be a loving and doting grandpa and hopefully will be really close to his daughters and grandchildren and find love and contentment in that.