I was a huge Dak fan his first year. I agreed with the decision to keep Romo on the bench because Dak was doing so well.
But hindsight is 20/20. I do think the Cowboys would have gotten pass the Packers had Romo returned as quarterback, but that's neither here nor there now.
Back to the question. If Dak showed more consistency, if Dak shows more accuracy, if Dak guides the team to score a game-winning touchdown in the playoffs, or better yet, in the Super Bowl, then, yes, I say break the bank for him.
But if he's essentially a bus driver, then, no.
Here's Dak's problem: he has a great team around him, particularly a great offense. He can't be average. Any average quarterback likely can win with this roster. Zeke, Amari, Gallup, CeeDee, Tyron Smith (1st rounder), Lael Collins (should have been a 1st round pick), Zack Martin (first round pick). There really is no excuse not to drive this offense into the playoffs, at the least. Dak has to go beyond that - both in the regular season and the post season.
You can't score only one touchdown and no touchdowns in games with an offense like this. You simply can't, not as a quarterback. That's what happened with Dak at the helm last year against the Patriots, the Saints and the Eagles.
So, if Dak shows himself to be average, then you look elsewhere, or at least be open to the possibility. Ideally, you want a franchise quarterback. You're always looking to improve your roster. And a franchise quarterback (though rare to find) makes up for a lot when your roster is thin elsewhere. Average to good quarterbacks need stacked rosters.
That's my two cents.