On one hand, it does suck that he's missing out on seeing the people he saw in the first cycle at least once before they die. On the other hand, if he really were to go around visiting everyone he's ever met, he'd be going in circles. Kaeha and the dojo were a special case.
I don't think his late friends would want him to end up in a cycle like that. The real question though, is how good his memory is.
As the saying goes, every person dies two deaths: once when they physically die, and again when all memory of them is gone.