@rrainboa Custom content can get corrupted when transferring between macOS and Windows, for whatever reason. What you can try, if redownloading everything would be a burden, is zipping the files together, uploading them to a free filehosting site (Google Drive, Dropbox, etc.; or use your existing iCloud or OneDrive), and downloading the .zip to a new computer. Both Windows and macOS can compress and extract .zip files. Right-click to see the option in either OS.
If you don't want to make an account for this, you could try zipping a few files together before transferring them via USB. I've never tried this, so I have no idea whether it bypasses the issue with custom content being transferred. But if you do try it, please let me know whether it works.
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