For anyone curious, WinOLS needs to have its registration updated every 6 weeks/50 app starts. If you need to reinstall onto another Windows install, you can manually delete a registration twice per year.
I have had an extra registration accidentally used up when I had a Windows update. An email to Axel at EVC, and all was sorted out.
I just installed it on a virtual machine so I can RDP in from anywhere. Confirmed by EVC as a valid license usage scenario.