Port randomization is widely used in port scanners. By default, Nmap randomizes the scanned port order (except that certain commonly accessible ports are moved near the beginning for efficiency reasons) https://nmap.org/book/man-port-specification.html

The OSSTM testing methodology that should be used to test under the worst conditions is known environment, which is a testing approach that assumes that the tester has full knowledge of the target system or network, such as its architecture, configuration, vulnerabilities, or defenses. A known environment testing can simulate a worst-case scenario, where an attacker has gained access to sensitive information or insider knowledge about the target, and can exploit it to launch more sophisticated or targeted attacks. A known environment testing can also help identify the most critical or high-risk areas of the target, and provide recommendations for improving its security posture. The other options are not OSSTM testing methodologies that should be used to test under the worst conditions. Tandem is a testing approach that involves two testers working together on the same target, one as an attacker and one as a defender, to simulate a realistic attack scenario and evaluate the effectiveness of the defense mechanisms. Reversal is a testing approach that involves switching roles between the tester and the client, where the tester acts as a defender and the client acts as an attacker, to assess the security awareness and skills of the client. Semi-authorized is a testing approach that involves giving partial or limited authorization or access to the tester, such as a user account or a network segment, to simulate an attack scenario where an attacker has compromised a legitimate user or device.