I think the way he is phrasing this question is a bit misleading.... I think he is asking what is better for your team leading into the next season.... Going 8-8 and winning on a high, or making the playoffs and losing on a nail biter?
Basically he is asking whether your team will be in a better mental state having gone 8-8 and finishing the season on a win, but missing the playoffs, or coming into next season having lost a nail biter... Personally I think the answer is obviously having made the playoffs. No player is happy with missing the playoffs... that what they are playing the game for, to get to the SB and win... (and the money obviously, which comes with winning that SB).