The Windows version is no longer compatible with modern Windows versions.
The Mac version (I own both) was for PowerPC Macs.
I've already paid for it a third time, as part of a HOMM box set for Windows.
Good Old Games has produced a fixed version, so I could pay for it a fourth time, but running it in the VM still works.
> Good Old Games has produced a fixed version, so I could pay for it a fourth time
It probably wouldn't cost more than $1, given that you're clearly willing to wait for a sale.
Advertised price right now is $5 with "lowest price in the last 30 days" of $2.50. The bundle of all 8 expansion campaigns shows the same current and recent pricing.