The response to this makes me think it's an even smarter idea. If GMs overvalue picks even half as much as fans do, I'm even more sold.
Here are the #3OA, 2005-2015:
Jack Johnson, Jonathan Toews, Kyle Turris, Zach Bogosian, Matt Duchene, Erik Gudbranson, Jonathan Huberdeau, Alex Galchenyuk, Jonathan Drouin, Leon Draisaitl, Dylan Strome
...and here are the #5OA, 2005-2015
Carey Price, Phil Kessel, Karl Alzner, Luke Schenn, Brayden Schenn, Nino Niederreiter, Ryan Strome, Morgan Rielly, Elias Lindholm, Michael Dal Colle, Noah Hanifin
Obviously lots of superstars in there that are mostly only available through the draft (Price, Kessel, Toews, Duchene, Huberdeau, Draisaitl, Reilly, Lindholm)....but lots of duds in there too.
To my earlier point, if the sens hit on the picks we get superstars that we'll have difficulty surrounding with enough talent to build a contender. Karl at $11.5M would have sunk us. To stay in our budget, we'd be icing trash on other parts of the roster. So we might "win" the pick selection, but short of a new richer owner, I don't think we're winning the cup that way.
Alternatively, if one or both picks miss or give us just an average player, we'd be wishing we could go back and trade the picks when we had the chance.
So, you offer me a deal around a good young upward-trending cost-controlled player + a prospect with a high ceiling and good trajectory and a late 1st, and I'm taking it. Let some other team with deeper pockets see if it's Carey Price or Luke Schenn hiding in the #5 box.
Of course, trades like this never happen, and sens fans would absolutely revolt (even more than they are currently). But they're winnable trades. It's just not a very sexy thing to do.