Firstly, I don't think the core groups you've listed there are equivalent. MacKinnon, Rantanen, Makar are three superstars that are on the All-Star team probably every year for next however many years ... the Oilers have really two, McDavid and Draisaitl. RNH and Nurse don't belong in that conversation, both of those guys honestly probably aren't as impactful as Landeskog. That is a significant difference, if the Avs did not hit the jackpot with both of the Rantanen + Makar trades I don't know if they win the Cup last year, they might still be a couple of years away without both. Kudos to them for taking advantage of those two high picks and making hay, I mean they were not the only ones who could've taken Makar or Rantanen. That's just good management, scouting, and development. But they had 3 superstars and then made a series of great trades *on top* of that.
The idea of "spending too many assets on one player will cripple your franchise!!!" I don't necessarily buy either.
Lets just say for the sake of arguement for example that we had for example "overpaid" for Dougie Hamilton when he was available at the 2015 draft.
Lets even assume we totally bent over and massively overpaid what Calgary was offering and gave up the 2015 pick (after McDavid) + 2016 1st + 2016 2nd. That ultimately would have amounted to us getting Hamilton for the picks we used to get Griffin Reinhart, Jesse Puljujarvi, and Tyler Benson.
Would that "cripple the franchise"? No. They likely would've been far better off if they had actually done that.
Draft picks aren't some magical get out of jail free card, and the Oilers don't even draft that well in the first place. Holland last four 1st rounders taken in Detroit are worth what today? Nothing as they're all basically waiver wire fodder. Most draft picks outside of the top 10 don't make it as impact level NHL players and even plenty of top 10 picks go bust (hello there Paajarvi, Yakupov, and Puljujarvi!). Now if you have really great scouting, that's one thing, but when you plainly don't, stop treating every pick like it's the next freaking Lidstrom. It's more likely it's the next Rassmussen, Puljujarvi, Yamamoto, Benson, Cholowski, etc. etc. etc. etc. etc. especially when these picks should be no where near the top 10 anymore as the Oilers should at bare minimum be a playoff team.