The other consistent thing is that those teams end up regretting it pretty often.
I don't think that's really consistently true. DeBrincat went way too late, and Broberg, Turcotte, and Soderstrom ahead of Caufield didn't work out, nor did Bennett/Da Colle/Virtanen/Fleury over Nylander and Ehlers, but there are lots of counter examples too.
For instance, I don't think the teams that drafted Cozens, Zegras, Seider, and Boldy ahead of Caufield regret their picks. I don't think Anaheim regrets taking Mintyukov over Nazar, nor does Chicago regret taking Korchinski ahead of Savoie. In 2018 Hayton, Hughes, Boqvist, and Bouchard all went before Wahlstrom (who was consistently ranked in the 5-7 range and above most of those D) and it worked out well for every team that passed on him.
I realize these aren't all exact 1:1 comparisons to Benson/Catton/Caufield etc (and I also realize those three are quite dissimilar to each other) but almost every year there's a high scoring smallish winger that we all fall in love with online and talk about as a top 5 talent who then ends up dropping to the 10-15 range. All of this is to say I don't think we need to think about this year as our last chance to get a forward like that, historically those types of wingers are available from 8-15.