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Silent Hill looks like a normal abandoned town if you have your shit together and aren't looking for your dead wife or some shit, so they just drove in and delivered it and he paid cash and then the driver left
"but the roads are all fucked up" not if you aren't struggling with the trauma of being assaulted by someone you trusted that manifests as a fiery anger against all things they're just normal and you can leave
He lucked out and found a pizza guy who was there struggling with his own shit
I found a YouTube link in your post. Here are links to the same video on alternative frontends that protect your privacy: