I am bit by the "recently upgraded or re-installed operating system" pretty much every time I run Hero-Lab (I need the software a few times a week, and I get new windows builds a few times a week). I understand the level of annoyance I get is going to be a corner case, but I'm hoping you all will makes some usability improvements to how your DRM works that helps everyone.
Some UX level ideas:
1) Put the Please Note! dialog earlier, say right at startup , rather then after checking for updates, choosing the game system compiling the data files, seeing the release notes, and dismissing the new char \ load char dialog.
2) Streamline the reactivation process from the Please Note! dialog:
2a) Add a Reactivate Existing License button directly, rather then making me find the "Activate Hero Lab License" page and then clicking it.
2b) Skip the "Retrieve" page unless you are missing information, or it failed to activate.
2c) When you do all this earlier in the startup, you can also skip the "Restart" question, and just do it. Another possibility is to move this dialog into a checkbox on a previous page (defaulted on if you are in demo mode since you can't avoid data loss).
3) Go ahead and do all this for me automatically
Longer term:
1) Find a hardware\system id that isn't messed up by Windows 10 upgrades
2) Consider becoming a windows store app via Project Centennial (https://msdn.microsoft.com/en-us/windows/uwp/porting/desktop-to-uwp-run-desktop-app-converter)
Thanks
--Ari
Some UX level ideas:
1) Put the Please Note! dialog earlier, say right at startup , rather then after checking for updates, choosing the game system compiling the data files, seeing the release notes, and dismissing the new char \ load char dialog.
2) Streamline the reactivation process from the Please Note! dialog:
2a) Add a Reactivate Existing License button directly, rather then making me find the "Activate Hero Lab License" page and then clicking it.
2b) Skip the "Retrieve" page unless you are missing information, or it failed to activate.
2c) When you do all this earlier in the startup, you can also skip the "Restart" question, and just do it. Another possibility is to move this dialog into a checkbox on a previous page (defaulted on if you are in demo mode since you can't avoid data loss).
3) Go ahead and do all this for me automatically

Longer term:
1) Find a hardware\system id that isn't messed up by Windows 10 upgrades
2) Consider becoming a windows store app via Project Centennial (https://msdn.microsoft.com/en-us/windows/uwp/porting/desktop-to-uwp-run-desktop-app-converter)
Thanks
--Ari