And Jay is entitled to criticize said moves as well
I think the point is...Jay and Drake think and move way differently. Drake is an actor... Jay is a hustler (if we look at their core from when they were 16-21)
Drake is used to "signing here and collecting money for a service"
Jay is used to "buying and selling" (whatever that means... selling drugs, starting a label, starting a clothing brand, buying and selling)
They won't ever see eye to eye because of their core values being misaligned. Drake might go down as the highest hip hop earner ever...but he made his bosses MORE money... Jay might go down as the highest hip hop earner ever, and he did it on the strength of his own endeavors, partnerships, owning his masters, etc.
which is correct?

I lean toward the Jay side personally...but Drake is making money with potentially less stress, less personal liability, and less effort. Jay is always moving and concerning himself with the next "flip"