I think Will would make a great dad, because he would be careful to be the things his father wasn't. (Such as, you know, THERE.) And I think he'd be happier not to be alone. Not to shock you or anything, but I can totally see him with Jack in this little scenario. A much older Jack, retired from pirating. Meanwhile Elizabeth has taken over the Pearl and is terrorizing the seven seas, and Will and Jack happily raise the kids she really doesn't want much part of...