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I don't doubt that the hardware itself isn't the issue; the problems only occur with Heroes 5. Regarding the disk error, other games from the same folder launch and run perfectly fine, and Heroes has been reinstalled multiple times, possibly even on a different physical disk, which is labeled as F in the screenshot. However, the error is always the same.
Here's another option I remembered: DxWnd is a utility for launching problematic old games on new systems, in windowed mode and more. You can add the Heroes executable to the list, right-click on the game in the list, and either run it or modify the settings in the DirectX tab. You can also enable logging to capture errors.