I just recently installed Chessmaster 9000 in my Windows 10 box, although I haven't used it to verify that all features are working. I made several posts in the following thread related to the installation, but I thought it would be better to start a new thread so that the information didn't remain hidden in the previous thread:
https://www.chess.com/forum/view/general/software-chess-simulators
Starting a thread to document attempts at getting Chessmaster 9000 installed in Windows 10...
(EDIT on Feb 3, 2021) - For later readers of this thread, the cause of the problem was found to be the Setup.exe file on most versions of Disc 1 of CM9000. Most versions of Setup.exe are copy-protected, and Windows 10 has dropped support for this copy-protection. My Disc 1 just happens to have an earlier version of Setup.exe that isn't copy-protected. @sangahm was the one who found the solution, which is discussed in Posts # 149 through 151, and in 186 & 190.