So I purchased Clinchfield Railroad from playstation.com, but it is not "checked" like Long Island Railroad. Yet Clinchfield Railroad is listed as "purchased" (since I bought it). How does Clinchfield Railroad become "checked"?
Did you actually install Clinchfield? Sometimes people buy it without installing it by accident because it doesn't install automatically sometimes. Is there a button to install somewhere (not in-game)?
The checkmark only appears when something is actually installed, so you will need to go to your library to install it manually. If it doesn't appear in your library you'll need to use the restore licenses option which should fix that issue.
