"Is there a limit on the maximum number of ORs, or am I missing something that looks right in my face?"
No no. The reason is because you have a hidden character:
$key == "transmission" or ? <= right there

What is 
Be unicode character ZERO WIDTH NO-BREAK SPACE .
Rewrite:
if ($key == "listingURL" or $key == "interiorColor" or $key == "engine" or $key == "transmission" or $key == "stockNumber" or $key == "VIN") {
Sidenotes:
As from the comments :
I will confirm this as the correct answer as soon as the deadline expires! Thank you so much for your help. I am using Sublime Text 3, is there an easy way to detect these hidden characters? - SoWizardly 19 min ago
For Notepad++ there is a plugin named: HEX-Editor .
You can download it through: Extensions → Plugin Manager → Available. Just set the combo box for the HEX-Editor and click "Install." After that, you can change the appearance of the file to hex.
There is also a plugin for Sublime Text that does the same.
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