I can barely remember a time when the Wings weren't in the playoffs. I'm not that old, but still. Missing would be a huge deal to me.
I can't rationally consider bottoming out because it rarely works, and talented prospects still take years to make an impact. Not to mention, the Wings are already great at drafting. Larkin is arguably the best player out of his draft. Nyquist and Tatar are playing like quality top 6 forwards. This isn't an old old team getting worse every year. If anything, the team should only improve as they graduate more prospects and develop the young guys already on the team.
I do think, though, that it's time to cash insome of our chips. Use some of these prospects that are good, but can't beat out other young guys for someone established. Go out and get a top line defenseman, or a high scoring wing. There simply aren't enough spots for everybody to make the team, and there are single player upgrades that could make a big difference to the teams play.