Well Ryan's run through bootcamp was...difficult. His mother and I are bearly on civil terms so I got all the letters (snail mail, came every Thursday) and his mother got the three or so phone calls so she wouldn't have a fit.
Ryan hated boot so it was always work to keep him upbeat all that. I tend to be very very long winded in letters. He regularly recieved four or five page letters, I usually had to be happy with a paragraph (which is loooong for him).
It's good that your bf is happy about his decision, that makes it a bit easier.