I have been using cakewalk since it's inception over 20 years ago. All I use it for is editing preexisting midi files as I know longer write my own since there are so many great sequencers out there like Trantracks and Midi-hits. I purchased Sonar years ago but gave up trying to figure it out. 
 
I run cakewalk 8 Pro on my old laptop with XP installed. Sooner or later I will have to purchase a new laptop and will no longer be able to run XP. My brother told me he found a way to install Cakewalk 8 Pro on a windows 10 platform but can't seem to get him to tell me exactly step by step how to do this. Is he pulling my chain or is there a way to do this? I have a Mac computer and set up a partition for Windows 10. That would be a great place to start and if worked could purchase a new laptop for live performance. 
 
Hope someone out there can give me advise.
 
Thanks
Donny

You could try and find out for yourself. You could do the same thing with Sonar Artist and it would be up to date and it for sure will run 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.
 
Good luck!
 
Hope this helps,
-- Ron