I responded to another similar post on the last page, yes some certainly teams do but I also don't think we'd be able to trade Caufield for Boldy, Seider, Cozens, or Zegras right now. I think Detroit, Vancouver, and Arizona might regret skipping on Benson at the moment, but I'm also personally not trading Reinbacher, Michkov, Leonard, or Dvorsky for him. They don't all end up like Benson and Caufield either. Wahlstrom was also a "steal" at 11 in 2018 and now Bouchard is a PPG defenceman & cup finalist and Hughes won a Norris while Wahlstrom has been a total bust so far. Ottawa got a lot of heat for Sanderson at 5 in 2020 but they sure don't regret skipping on Perfetti, Rossi, Holtz, and Quinn for him.
Regardless my point is not that skilled smallish/non physical wingers are "bad" as a blanket category or that we shouldn't consider Catton or anything to that effect, it's that in actual reality they're almost always available later in the draft than publicly available lists would suggest, and also that we remember the Caufields and forget the ones that didn't work out.