To me the ideal package would be: 1-2 Contract players; 1-2 1st round picks and at least 2 top tier prospects. One of the players going back to Edmonton should be a goalie.
That’s realistic, but Edmonton fans would likely be disappointed (at least initially) with the quality of those players and prospects.
For starters any team that trades for McDavid with two years left on his deal is looking to win a Cup in the immediate future, so they aren’t going to gut their roster of its top players to do so - especially if said players are on reasonable longterm deals. Maybe a team like Toronto that also has overpriced stars with little term remaining would swap one to upgrade, since they don’t have the cap flexibility to add McDavid outright, but then the bulk of the value in the return would be short-term which isn’t conducive to the rebuild that the Oilers need. Or you might get one or two good but moderately overpriced complementary players with term back. But you aren’t getting an elite player with term on a good deal for only two more years of McDavid.
As for the goalie, again any team trading for McDavid is looking to win now, so you aren’t getting their best goalie. At best you’re looking at the 1b in a 1a/1b situation, or maybe a veteran starter with a highly touted prospect behind him who makes him expendable. Now if you’re willing to take a prospect goalie rather than an established NHLer you’d have more options, but that would of course be a bigger risk (on the other hand you could potentially end up with a better goalie this way - you pays your money and you takes your chances with this approach.)
And as for the prospects, in a cap world nobody is giving up a truly elite prospect who can contribute at a high level on his ELC and be under several more years of control after that for two more years of McDavid. First of all the sort of team looking to trade for him is unlikely to have such a player, and the teams that do are likely rebuilding and in no position to trade for McD. If somehow a competitive team does have an elite prospect, that player would be more valuable to their Cup chances contributing on his ELC than McDavid would be at $12.5M. So again, you might well get a competitive team’s top prospects, but they won’t be truly elite ones.
At the end of the day the return isn’t going to wow Edmonton fans - at least not right away. The hope would be that the picks pan out and that one or more of the players/prospects ends up surprising to the upside, which has been known to happen (the Lindros and Eichel trades come to mind.) But the masses of Oilers fans who fantasize about getting established elite players with term back will be sorely disappointed.