Xbox 360 on Windows 10 ?
If you want to solve this problem once and for all sadly the only option is to reacquire a PC version of the games. I know these days Microsoft has been a lot better about giving you a PC + console copy when you buy a game through them but I'm not sure if that deal applies retroactively to old titles... I assume not. Another option is to just get another xbox 360 or newer console that's backward compatible but that doesn't solve the problem, just pushes it further into the future. If you do go with the PC option, as a bonus, the games will look and run better, as well as be more convenient (no more optical media).
Slightly off topic but one thought I just had is it would be super nice if Microsoft released an official emulator for consoles that are no longer supported (anything that's no longer covered by a currently sold model or backward compatibility of said model). If they did it, it would eliminate any issues of legality, as well as provide, conceivably, the most reliable and well-performing experience vs anything a third party could make through reverse engineering. I don't think it would be unreasonable to expect it either, Microsoft has always pushed hard for backward compatibility across the board, often even to the detriment of other things. Particularly if they charged for it rather than just providing it with Windows 10, it would be a good way to squeeze a bit more money out of what's otherwise a dead platform while simultaneously providing a desirable and good experience to users.
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