With the update that added the wing suit, this achievement has been made considerably easier.
Once you have access to the highest supply point in Elizabeth Niemand's tower, simply fast travel to it, equip the wing suit, then jump off the tower and press
to activate the wing suit. Head towards whichever Propaganda Tower you wish and aim for the topmost platform and try to land on it.
In my experience, even if you miss, you'll likely trigger the checkpoint. In this case, you can just free-fall and hold
to restart right next to the console that you need to interact with to capture the tower.