My take...
The timelines are different. Jack needs / wants Champions League football now, in the peak of his career. Villa do too, but we're a decade behind City, United, Chelsea and Liverpool.
An NBA team who gets first pick in the draft, generally does so because they were the worst team the previous year. The first pick might be a generational talent, who wants to win it all. Realistically it will take that team a long time to build a roster around him to be able to compete with the mainstays of the league.
We can't move forward as fast as Jack needs us too. Our progress has been phenomenal since NSWE came in, but this step up now to consistent European football will be the hardest and take the longest. Jack doesn't have the same amount of time to waste.
If he goes, I dont blame him. We're both on upward trajectories, his is just faster than ours. Chukwumeka, Ramsey x 2, Barry and Bidace might be the right players, at the right time, to grow with us. Not out grow us.
Time will tell.