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Is it illegal to enter and leave Macao frequently with a work permit?
Not illegal.

The Macao work permit is only a permit to work and live in Macao and is not used for customs clearance. But the endorsement on your Hong Kong and Macao Pass for working in Macao is multiple round trips. During the validity period of the endorsement, you can travel freely to and from the mainland, even multiple times a day.

Mainland residents who go to Macao with a stay endorsement apply for a stay endorsement again during their stay in Macao or after returning to the mainland, including the replacement and renewal of the Hong Kong and Macao Pass. Those who meet the requirements of the Ministry of Public Security to apply for Hong Kong and Macao Pass and endorsement in the place where they are not permanent residents can apply to the exit-entry administration department of the relevant local public security organ according to the regulations.