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Useful tips

You can take pictures of the billboards using the phone: by taking a picture and then uploading it to the Social Club, or simply by taking a screenshot (better resolution). (G to hide the grid)

You can take the pictures in story or online mode, but the easiest way is to use the director mode which allows you to teleport, change the weather and the time.

If it is difficult to take a picture of a billboard from the front, you can record a short clip (F1) and take the picture by editing the clip in the Rockstar editor. (H to hide the interface)