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Less denotes amount, quantity, value, or degree, fewer denotes number. We may have less water, less food, less money, less education, but fewer books, fewer letters, fewer friends.
We say less than (five, six, etc.) pounds because the pounds are considered as a sum of money and not as a number of coins.
All meaning everything, takes a singular verb, all meaning everybody, takes a plural verb: All of us are present.