Enterprising simply means successful and that is what Gates is, whether people like it or not. Personally I don't find it necessary for individuals to possess so much money but if they make it to the bigtime then good luck to them.
One of the beauties about Windows is that it provides installation instructions that my great gandmother would understand and Microsoft is to be commended for that, it's the one thing that has brought computing to everyone. If you get most Linux/Unix OS's you cop the "Select your video card fromt he following list and stiff sh*t if we chose not to bother supporting it" - With Windows you see "Windows is now choosing the best video driver for your card, please wait a tick" - clearly indicating that to install Windows requires no prior experience.
Windows has it's problems and to list them all here would be just doing so for the sake of arguing silly points. The fact that Microsoft has chosen to make life easy for those that want to enter the home computing fraternity looks pretty enterprising to me.
Looks like Her Majesty agrees.