Does the Hong Kong and Macao Pass have to be stamped with a red stamp every time you go to Hong Kong?

No. The Hong Kong Immigration Department has the right to verify the passes and endorsements. If you go to Hong Kong after the Hong Kong and Macao Pass has a red stamp, you won't be checked. You just need to brush it. The People's Republic of China Travel Permit to and from Hong Kong and Macao (commonly known as the One-way Permit) is a document issued by the Exit-Entry Administration of People's Republic of China (PRC) and China (that is, the National Immigration Administration, one institution with two brands) to mainland residents to settle in Hong Kong or Macao.