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if we are to keep the ps 500 words or less, does that mean keep it under two pages, or literally keep it under 500 words using the word count function?

If it says exactly "500 words or less" that means word count, not page count. Better be 500 or less.

It means your adcomms are tired of reading wordy PS and will be pissed off if you try to sneak a longer PS past them.