I figured it out y'all. The game has a serious bug where the entire chain of events get skipped if you don't click each thing in the right order.
1. Exit the vault
2. Click the question mark.
3. Click the diner. (South)
4. Go back to the question mark.
5. Go directly Northeast to the building that kind of looks like a fort.
6. Do the event and go far east to the radio tower.
A lot of events will now make sense and you won't miss any interactions!