Not really that bad for Winnipeg. The 1st should be, should be, a late first. The likelihood that a player in the late first becomes a difference maker is well documented as being pretty low. However, they would be expected to be a contributor if they make it to the NHL. The disparity from the top 1/2 of round one to the entire rest of the draft is pretty dramatic. Not a perfect science but it seems common to indicate a contributing player needs 2-3 years to show they are a contributor and solid NHL player. You can roughly track that by looking at games played and draft position. If you go back to 2016 here's a rough breakdown:
2016 - (300 games played) - Total (YTD) = 21 players. 11 from the top 16 of the draft, remaining 10 from the rest of the draft (3 from the balance of the 1st round)
2017 (250 gp) - Total = 18, 8 (top 16 in draft), 10 from rest of draft (4 from bottom of 1st round)
2018 (200 gp) - Total = 16, 9 (top 16), 7 (balance, 4 from bottom of 1st)
2019 (150 gp) - Total = 12, 9 (top 16), 3 (balance, only 1 from bottom of 1st)
2020 (100 gp) - Total = 14, 9 (top 16), 5 (balance, 4 from bottom of 1st)
That's not to say there aren't others that play NHL games but this would seem to be a reasonable expectation for games played to at least be a regular contributor in the NHL. Late bloomers, non North American players will impact the timelines but most scouts will tell you it's reasonable to expect an NHL player to be playing within 3 years of their draft year and developed by 5 years post draft. All this to say, a bottom half 1st round pick is still a risk to even contribute at the NHL level. Worth the risk much more than after the 1st round, but still really need to be picking in the top half of the 1st to have a higher probability of success.
We see "1st round pick traded" and gasp. Unless it's the top of the 1st round, it's still a bit of a crap shoot. Again, better than a pick from any other round but not the Ooohs and Aaaahs we might build it up to be. It's a fair deal for both sides.