The opportunity would present itself in those situations, but Jerry Jones has not pulled that trigger historically. The only occasion that kinda matches the circumstances was 2001.
However, Dallas did not have a first round pick that offseason and used its second round pick on Quincy Carter. It should also be noted Jones pulled that trigger after losing Troy Aikman AND acquiring Tony Banks to ensure Carter would receive more time in assuming the starter role. Of course, Jones ditched Banks at his earliest opportunity. He is a professional football mastermind.
Opportunity is one thing. Hoping Jones will cash in an opportunity is totally different.