I have countless playthroughs in it. Definitely over 10 complete runs at this point and I'm currently doing another during my vacation. The game has things I'd change, but it's awesome regardless and I love the gameplay and the world.
The story content is good, but at 10+ playthroughs I focus mostly on the Gigs, the green missions, which are more gameplay heavy. The Main and Side jobs tend to pack more story moments in them. The game needs radiant missions, if infinite missions in this game were a thing, there's so much that could be added to the game design.