Tampa and Vegas had major advantages with their manipulation of LTIR by making moves to bolster their lineup with the LTIR space then having the luxury of bringing back their best forwards for the playoffs, icing a team $9-$10 million dollars richer than all the other playoff contenders. I don't blame them for that, I put that on the league. They had very good teams either way but it sure helps to add a Kucherov and a Stone to an already capped out team.Holland definitely lacks creativity but you must see the differences in at least Vegas from Edmonton. Virtually every significant deal that Vegas had made would not have been possible for the Oilers because they involved players that had NTC/NMC or that were pending free agents who would not resign with the Oilers or were made possible by LTIR moves that were at the very least dubious. The LTIR moves are not something you can just do. You need the right situation.
It's been quite a while since Tampa made a creative deal that made their team better. Mostly they have been shedding depth and paying more than premium prices for players. Like Vegas they had a massive advantage in that players were eager to go there and even to sign at a discount.
With Colorado I don't see a lot of creativity in their deals. They had benefitted from MacKinnon's contract being just a hair over half of his actual value but now they are paying the price for that. They had to take a massive hit to their depth after winning. This year they are using their LTIR on Landeskog to add Johansson but that does not make them a better team than if Landeskog was healthy. Before that the most impactful trades they made were Lehkonen for a 2nd and Barron and
Toews for 2 seconds. The latter trade was a home run but it was not really creative. The former was pretty much a standard TDL trade.
As I said it is perfectly reasonable to be critical of Hollands lack of creativity with the cap. But comparing the Oilers situation with these three teams is not really helping the case.
It helped that they're desirable locations especially in Vegas's case but it also took some cojones for Vegas to pull of the moves they did.
Colorado did benefit from the MacKinnon contract, although we can argue that the Oilers benefitted from the Draisaitl contract but they made a lot of savvy moves to build that roster outside of the homegrown guys. The Toews trade, as you mentioned, was a masterclass. It was their Ekholm trade but better because Toews was younger and they saw the potential in him before others did then locked him up to a ridiculously good contract although they're going to pay the piper soon with him.
The Duchene trade that netted them Byram and Girard. Brilliant
The Barrie trade that netted them Kadri. Great
Taking a chance on Nichushkin. Perhaps a bit of luck but...brilliant
Manson trade was solid, Lehkonen trade was great
Maybe nothing super creative in terms of cap management but absolutely brilliant moves that shaped that Cup roster.