Re: Cakewalk 8 pro on windows 10
If it were me, I would try to install Cakewalk Pro 8 in "Compatibility mode" and select "Windows XP". You can access Compatibility settings by right-clicking on the Cakewalk installer and select Properties from the context menu. The "Compatibility" tab at the top of the Properties window contains a Compatibility troubleshooter and allows you to manually set the version of Windows that your software needs to run. There is more information on "Compatibility mode" on the web, so Google is your friend.
I would also recommend you run the installer using the "Run as Administrator" option.
There are no guarantees that my suggestion will work and may take some trial and error, but I have successfully used this method to install "obsolete" drivers and applications that would not install and run correctly on Windows 10 without Compatibility mode.
Hope this helps,
Sonar Platinum x64 2017.06, X3E, X2a, X1d, 8.5
Windows 10 x64
AMD Phenom II X4 955 3.20 GHz
8 GB Ram
Nvidia GeForce 9500 GT
Echo Gina 3G