Based on your answers, you need what Windows 9x/Me offers OR you do not wish to take the trouble to get anything else. My recommendations, in order are

  • Windows 98 2nd edition if you can get it
  • Windows ME if you are getting a new machine and the manufacturer does not give you the option of Windows-98 2nd edition
  • Windows-98 original or upgrade
  • Windows-95. Be sure its release date is 8-24-96 or later. Otherwise you don't get FAT-32 support and cannot make good use of today's hard drives. Keep in mind that USB support doesn't work well in 95.

    • Now the only question is whether you need a dual-boot machine. If you have security needs or are bothered by computer crashes, then you'll need to go back and see if they are better addressed by another operating system. If they are, then you need a dual-boot.