Yes, for several reasons. First, I don't trust the front office to acquire a good QB in a decent amount of time. If we are going to go into rebuild mode, I'd rather do it after Dak's next contract. This FO will do something dumb like Shadeur Sanders, who is basically a worse Justin Fields, and we'll really be in purgatory for several years. Even outside of this FO's historical ineptitude when it comes to high round QB's, just in general it's statistically one of the hardest things to do to actually hit on one in the NFL. Dak has shown that he can make all the throws and has stretches of play where he can play as good or better as the best in the league. I can't explain his playoff no-shows. I have no idea what's going on with him, and it's gut wrenching to watch. It's unacceptable for a QB paid that much to play like that in those moments. But, I believe in Dak's character and his competitive drive, and I think he will do everything he can to turn it around and win.
I think his experience and tenure is also important. Those years of learning and knowing the game are valuable. I don't know about the rest of you guys, but I get better at my career every year because I know more and have applied it more than I did the prior year. Dak's not a WR or RB who loses his legs after his 20's are over. He's a QB and can continue to improve and grow. We're all sick of the playoff implosions. But, when considering ALL the variables, especially with this team/front office, I think Dak gives us the best chance to win even with the baggage. Even with the multiple playoff losses. The rules of variance dictate that he can turn it around and get hot at the right time one of these years. Also, I never thought I'd say this, but if any team is equipped to manage three max deals, it's a team like the Cowboys who build primarily through drafting well and being (comparatively) cheap in free agency.
The problem is that this is a very nuanced answer. People want to read the "yes" as "Dak is the best QB in the league and will definitely win a super bowl and we should ignore all the playoff losses, Dak is god and can do no wrong and deserves $65m a year, etc. etc." It's just not that simple, and I still remember the period between Aikman and Romo and how horridly miserable that was. The QB market is what it is, and I'd prefer to take one more shot with this core group.