Comment by occz
4 hours ago
Upgrading when multiple versions behind is significantly more risky than doing it when the update is relatively fresh.
Additionally, actions done frequently are less risky than actions done rarely, since you develop skills in performing that action as an organization - see high deployment frequency as a strategy of managing deployment risk.
This adds up to continuous upgrading being the least risky option in aggregate.
Not if software regressions are the main concern.