I think Prescott's main issue wasn't that he was a 4th round pick but that he seemingly hid behind his agent.
It's an old story that Romo negotiated a contract with Jerry first hand. Jerry really respected the confidence and agreed terms. Didn't Lawrence end up picking up the phone to agree a deal with Jerry/Stephen last year?
I think had Dak simply negotiated directly with Jerry at some point that they would have thrashed out a deal where both would have moved a bit. E.g. a 5 year deal and a bit more guaranteed money at around $36 million a year.
I also think that Prescott genuinely wanted to stay a Cowboy long term but he positioned himself into a corner and stayed there rather than coming out of his agent's shadow.
I do not rate him as a quarterback and in my view, longer term it is excellent news for the team to not be saddled with a huge contract for an average yet exceptionally durable player. However, looking at it objectively it's quite sad and I think he will look back in a few years and regret how he went about it.
Also, a lot of what I post is tongue in cheek. I know there will be people very disappointed at the news given a player they have really taken to is unlikely to be playing for the team beyond this season. I respect that but I genuinely think it will work out better for the Dallas Cowboys and Dak will get his elsewhere longer term.