This is exactly what I've said numerous times. It was NEVER the plan for Dak to be a starter in year 1, nor year 2, or even year 3 probably. He was what so many cry and whine about on here and elsewhere that the Cowboys don't do - draft a developmental QB. But the perfect storm happened.
In today's NFL, teams get on a roll and can ride that to the Super Bowl. The Cowboys were in that situation with Dak and I won't fault them for staying with him. Too many people make the leap that a different decision would yield better results. I've seen it posted often and loud that we beat GB if Romo was the QB. Maybe, maybe not. There's no way to know. That game was lost by the defense the same as in 2014. Maybe, just maybe a case can be made that they should've gone back to Romo before the 2017 season. But Romo was not the future and was waaaay nearer the end than being in the "prime" and it seemed they did have the future (and may still, but that's for another thread).
Now, to the question posed in the thread title - yes, we are better today than 8 years ago. But, as with any corporate leadership, the style and skills needed differ as an organization grows or markets and economies shift. At this point, Garrett may have served his purpose and it's time for a change. However, it's highly, highly unlikely in my opinion that a change will actually produce better results simply because of Jerry and past history. There is no stadium on the horizon he needs to get approved so a Parcells-like move is not likely. He said at the time after Parcells was gone that time was the least fun he ever had and he wouldn't do that again (paraphrasing). The only hope is that Stephen and Charlotte wield enough power and legitimacy with Jerry for him to relent. Stephen is not perfect, but I don't sense that his weaknesses are that he needs to be in total control or is an egomaniac.