You're wrong about picks having specific values, this years draft is known to be not as deep as next year, 2005, 2008, 2015, and 2020 were all very strong drafts, while 2011, 2012, 2014, 2021 were less so, decisions need to consider that context. 7 OA in 2022 had a set of available prospects to weight against the asset coming back. DBC imo was too big of a risk to walk so it was a bad trade, but for another player, it may have made sense.
You're completely ignoring the context, Winnipeg absolutely needs to show it's players they are serious when they are in a rebuild stage if they want to retain or attract. If they had missed the playoffs for 7 years straight, they'd need show upcoming UFA that it's worth sticking around if they didn't want to sell off, but when they are a top team, the context is different, and they can show the players and UFA they are serious through making the tough choices. Context matters.
I'm not talking about one bad pick, I specifically said even if we'd made a better selection than Boucher like Sillinger in 2021 we'd have likely been better off trading that pick for someone in the vein of a Fiala type asset.
Winning sells tickets, I agree. Waiting around 3+ years for a pick to develop doesn't help win or sell tickets for 3+ years, if ever. Small markets can only withstand so many down years before things start to give. Current management has the luxury of an influx of money and good will to a new ownership group that allows them to be more patient, that wasn't there when Dorion was making trades, in fact, it was the polar opposite.
Taken to the extreme, your hard and fast rule of don't trade 7OA when rebuilding would mean Boston shouldn't swap 7oa for Dahlin, Q.Hughes, or B.Tkachuk, but they'd be crazy to turn any of those offers if they were on the table. You need to weight the potential of the pick, against the impact the incoming player will have, both directly on the ice, and indirectly through things like making the team a more attractive destination and aiding in the development of the kids.