Is it permissible to reinstall the operating system to obtain a new trial period for software, and is it permissible to earn money using trial software?

It is not permissible to infringe upon programs whose owners have not authorized their use, because they represent a protected financial right. What the questioner is doing is an infringement upon this right. There is no difference between breaking protection or downloading the program multiple times; both are committing a forbidden act through deception. If the use of these programs for personal benefit without the owners' permission is prohibited, then it is even more so that trading in them is prohibited.