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Let's go back to the basics - are you working in the right folder? In the main HL window, in the Tools menu, choose Explore Folders, and then Game System Data Folder. That'll open a folder from your computer - is the file you're creating this content in within that folder (and not a sub-folder)? Having a file somewhere else is something that can create the symptom of things only working after test now - HL only loads files from the correct folder when loading, but the test now operation just patches that one item into the database, and where the file it's from is located isn't checked.
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