The DOSBox flag mean that the game been tested in DOSBox succesfully. The XP flag mean that the game been tested in XP successfully. For the boot disk, I don't think it limit you to use the program only in DOS. It's only a gateway to take you to the default boot disk which would hopefully help you if you were to try to make the game run on a pure DOS machine.
Win98SE should be able to run 90% of all games (if you take for granted it's not made for a newer version of Windows) and XP should be able to run most games if you use VDMSound.
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