From a quick look I'm going to point out that those guys either took 3+ years to make an NHL team, or 3+ years before they started making a serious impact. While our first couple of drafts under Yzerman could have been more productive (though Wally, Albert, and Elmer could mitigate that a bit) I'm not sure it's time to write off our drafting beyond the 1st round yet.
It takes time for guys from rounds 2+ to make an impact, and the Wings it's more so right now because I think Yzerman has purposefully slow walked nearly everyone to help build up the farm.
Okay, you just drafted a guy a year ago with your top pick. You liked him enough at that point to spend significant asset collateral on him. Now, a year later, you want to turn around and deal him for another lotto ticket. Maybe you just really like someone in this draft, but it looks...fishy. It looks like you have soured on him, a lot, in the past year or two. If you're another team, you have to be wondering what that team has seen in this kid that it didn't see before to make them want to cut ties so soon. If, for example, NYI are looking at Eiserman and already going, "Yeah, nope." That's a big red flag for me.
Trades like Gibson/Kiskinen are different. You're swapping for known pieces, neither side is tossing a guy for what's in box #3. There's less reason to look at it and wonder what you're not seeing.
Also, I think our 1st carries more value in dealing for an established player than for a prospect. If there are no red flags, you're still paying for potential and no prospect that you can pull largely with a mid-1st is going to be great unless that other team is screwing up in some big way. I think we get more bang for a trade buck by going after an established player.