User blog comment:SlenderDev/Hardest GTA mission/@comment-22427681-20140711164153

Air Raid, Supply Lines (Zero) and Vertical Bird were the worst for me in San Andreas. I vaguely remember the mission in Vice City where you had to beat Phil Cassidy in a shooting range was also quite difficult at that time, maybe because it was the first GTA I played. These are the first that come to mind, I find 3D era games harder than HD games... in GTA IV & V there aren't many "hard" missions.