Yeah, Nill doesn't every overpay it seems, and tends to back out of over rich situations. Zuch was the exception, and done with the idea that if they made the PO, they could go pretty far. Same scenario, maybe with even slightly enhanced expectations, might result in a similar trade. And, TG can always step in and direct trades, as he did in the great sell off of 2012 with Niewy.
Interesting, but read a stat in another field (golf) where 2 golfers can average hitting approach shots to 20 feet from the pin, but the golfer who hits one 2 feet (and makes birdie) and 38 feet statistically fares better than the on who hits both shots exactly 20 feet and is likely to make 2 pars.
I think the same thing could be said for drafting. In 2017, the Stars were going to get the 8th and 38th pick. (Not counting their second first rounder, where they traded and got Otter) They did better with the 3OA (Miro) even if they had to move back or traded the second round pick, since basically, all the other picks are iffy to make the NHL, whether 23rd, 39th, 45th overall, etc. So, trading our mid picks, or even considering next year's 2nd and maybe even first can't be ruled out.
Hence, I think statistically, if you're going for it, you go for it, even knowing you pay somewhere down the road, like other Cup champs and near champs. Balancing now and the future by stockpiling picks seems to makes sense in general, and sounds nice, but may not be proven statistically. Not quite the same, a necessary player in hand this year beats a few in the bush a few years from now that may or may not pan out.