Depends on the makeup of the roster.
If you have an ageing roster with some good players and some holes, and your realistic expectations are to possibly get in as a wildcard, but would take a miracle to win it all, you're probably better off picking high in the draft.
If you have a younger roster with some legit up and comers and some holes, and your realistic expectations are to possibly get in as a wildcard, but would take a miracle to win it all, you might be better off playing for keeps and promoting the culture of winning.