Thanks for doing the research on pick trades, it's good to understand the context of how infrequently it happens.
Re: "it takes two to tango" though - could it be that teams in the top 10 are willing to move down and the missing dance partner has been the team willing to spend to go up? Not sure how many teams have been in the position we are in - entering win-now mode but dealing from deep, quality surplus with a strong young core established, #1 prospect pool with 4-5 forwards looking like sure NHLers in at least some form, and plenty of future picks remaining.
Not saying it would necessarily be wise for us to move up. In fact there might even be a case to be made for shrewd teams looking to move down in specific spots if the price is indeed so significant. I understand that the odds of selecting a quality NHLer decrease rapidly, but there might still be an inefficiency propped up by the egos of scouts and GMs who are positive their top 10 target is "the guy" when in actuality, plenty of selections from 11-20 end up proving better.
Let's assume Oliver Moore is the 13th pick. If you packaged him with Rosen for example, who does that duo trump in terms of expected future value? I'd say everyone not named Bedard, Fantilli, Carlsson, Michkov, and Smith. I'd rather have the duo than Dvorsky, Benson, etc (except Reinbacher for us, considering need and surplus). After the first five this year, it's a crapshoot and a team in full rebuild should value two cracks more than one.