You don't get to play asset management games with your own pending UFAs, not when you are even a modest buyer and a playoff team. You aren't going to trade them as rentals for futures at the deadline. Early in the offseason, you can re-sign them or see them walk in free agency. At no point are you going to be able to use them as trade chits.
But, ah, the moon shot that keeps HFBoards going! In the exceptionally rare cases where sign-and-trades have happened in the NHL, it's been about the player using his current team (which make no mistake, is signaling that it wants to be rid of him in these scenarios and maximize its return) to get the extra year that he can't get in free agency.
There has to be something in these scenarios for the player, which he can't get on his own. The moment a team comes to you and says it wants to trade you, it's not your team anymore. You'll just decline and tell them you'll call your own shot in free agency in a few months, and f*** you very much. They've given up the right to claim loyalty; they want to trade you and they've told you so to your face.
The upshot is that sign-and-trades are only applicable for superstars, for the sorts of players that teams would give eight-year deals. The eighth year, which a player can't get on his own in free agency, is what entices the player to play ball. That's it.
Anyone think Nugent-Hopkins is in line for a max-term deal? No? Then why does he help out the Oilers?
My guess is the Oilers re-sign him in the offseason, perhaps right after the expansion draft but before the start of free agency. My gut feeling is they'll probably give him more than the OP would like, but that's the way it goes with free agency.