The problem is we likely end up waiting for something that doesn't happen. Taveras hitting the market would be an anomaly compared with what usually happens with star players. And we haven't seen guys like Doughty, Karlsson, OEL, etc. hit the market either. It's probably far more likely that some or all of them are traded to new teams at some point next season (or even this summer) that can get a deal worked out than that they hit the open market.
I think if a guy like Taveras or Karlsson hit the open market we have to at least put a bid in. We might not win but the likelihood of getting similar players through the draft or free agency or fluke inter-dimensional travel is so low. If we can get a top5 at his position type guy I think we should do it. A 27 year old Taveras or Karlsson are guys we can build around for another 5-8 years. There's a very good chance we won't do better through the draft.
If you were Detroit's GM, would you trade a 3rd round pick for Tavares before the draft? With a condition that you'll trade them another 2nd if he signs?
If the Islanders accepted, what would you offer Tavares to get him to stay.
You can now offer 8 years.
So, let's say you get him to sign at 8 years, $12M.
Would you trade Mantha, and your second first round pick (18), Rasmussen, Nyquist and a conditional first (19) for Karlsson and Ryan?
You'd have this to start the season:
Zetterberg- Tavares Bertuzzi
Athanasiou-Larkin-Frk
Svechnikov-Nielsen-Ryan
Abdelkader-Glendening-Hlem
Turgeon
Dekeyser-Karlsson
Daley-Hronek
Ericsson-Jensen
Witkowski
Howard/Bernier
You'd still have whoever you draft in the first and second round in 18 (giving away the late first and Ottawa 2nd).
But you'd giveaway Detroit's first next year to keep Karlsson (and you'd need to find away to raise his pay substantially - though Howard's departure would take care of a lot of it).