lol PSP sales.
Anyway, with Laguna, I would say that he lived an amazing life, but not necessarily the happiest. Laguna spent most of his life without the people he loved most, his wife and kid(s). When you think about FFVIII in terms of a love story, that's pretty significant. Yes it was full life, and one with things most people could only dream about, but it was still absent of the things that made him happiest- his family.
I always got the impression that he became president not because he wanted to or because he loved the job, but because he had this overwhelming sense of duty. In fact, although he was usually happy go lucky no matter what the situation, he seemed only genuinely content with Raine and Ellone. His life eventually went on to more grandeur things but he would probably give it up in a second to go back to the simple times.
Don't necessarily see it as regretful, I don't think Laguna was the kind of guy to dwell on the bad. And I think he probably loved the adventure. But the very last scene we have of him, president of the most technological city in the world and co-savior of the world, is at his wife's grave with his adopted daughter- because that's what was really important. The time he spent and maybe the time he never got to have.
EDIT:
JFC Edea is fucking fabulous no matter what mistake.