Ownership's problem is that by now everyone knows the Wings aren't good. A bad team full of veterans on their way out draws as badly as or worse than a bad team full of kids.
Of course, their arena project was a case of hilariously bad timing. It's rare for a team in as bad a position as the Wings to open a new arena just as they enter lean years. They probably believed the Wings would always be good, and maybe Ken Holland told them that, too. The only way to avoid this issue would have been a drastic rebuild initiated around the time they started the arena project in earnest in 2012.