I hate trading draft picks (especially 1st and 2nd round picks) as much as anyone. With that said, the early returns on our 2nd round picks in the Brackett era has hardly been spectacular: Woo, Lind, Gadjovich. At the end of the day I think you got to strike a balance between relying on your draft picks turning out into drafted prospects who develop into good NHL players and using draft picks as currency to actually acquire NHL players.
Why'd you leave out Demko from your list?
I think there are really only two main factors for determining whether it's worth giving up draft picks (and I'm probably stating the obvious here): (1) is the player you're acquiring in the trade worth it?; and (2) what are the quality of the prospects who are available at the pick?
I'll try to demonstrate this with examples on each end of the spectrum involving trading away our 2nd round picks.
The Baertschi trade is one. This seems a bit more justifiable to me. We gave up 53rd overall (Calgary drafted Andersson); if you look at who was drafted from 53rd onwards, it's really just Andersson and Dunn who have become regular NHLers...and then we drafted Brisebois at 66th overall so there's not much of an argument that we could have drafted a player like Cirelli who went after Brisebois. It seems pretty unlikely that we would have landed either Andersson/Dunn, but we'll obviously never know the team's rankings for that pick.
On the other hand, trading 33rd overall in the Gudbranson trade was god awful, and not just because Gudbranson sucks. That 33rd overall pick could have been any of Kyrou, DeBrincat (rumour was the scouts liked him), Girard, Hart, Lindgren, Hronek, Dube, etc. Even lesser known names like Gambrell have developed well so far. In other words, there are at least 7-8 players who went within 25 spots of our 33rd overall. Those are some pretty decent odds at landing a quality prospect that is likely to be a consistent NHLer.
Not that this necessarily applies to you, but I'll never understand how some posters here can always commend management on their drafting capabilities, but then dismiss draft picks that are traded away by using the "well they barely ever pan out anyways" logic. Seems contradictory to me and likely is due to confirmation bias.