Crime Boss: Rockay City

These stories seem to be randomly assigned to you each run. In my experience, you only get 2 of them in a given run. In theory, you could speedrun the first few days of "Baker's Battle," testing which stories they give you; then restart if you didn't get the one(s) you were hoping for. I had to figure a lot of this out on my own with not a lot of explanation, so here's something that may be true, but I'm not sure: some characters need to be unlocked, and then purchased, in order to begin their mission chains. I am fairly confident this is how things are with Ranger specifically, because I completed his "Urban Legend," which made him available for purchase in "Baker's Battle." His first quest appeared after I purchased him for my team in a run. I'm just trying to be helpful to anyone lost like me - I don't have as many concrete answers as I would like.

This can be confusing if you don't know what to look for. When playing the campaign, background missions for five characters will randomly appear. These are marked in light yellow on your map (see screenshots below).

The story arc for Chase contains two missions: "Trespassing" and "The Predator". I believe he does not need to be on your team for them to appear. Once you complete the first one, the second will appear one or two days later and you will get the achievement after finishing it.

Below are screenshots of both mission markers for Chase. The location on the map is random, but this is what you're looking for.

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2.

This can be confusing if you don't know what to look for. When playing the campaign, background missions for five characters will randomly appear. These are marked in light yellow on your map (see screenshots below).

The story arc for Chase contains two missions: "Trespassing" and "The Predator". I believe he does not need to be on your team for them to appear. Once you complete the first one, the second will appear one or two days later and you will get the achievement after finishing it.

Below are screenshots of both mission markers for Chase. The location on the map is random, but this is what you're looking for.

1.
2.