I have four active machines all on different versions of Microsoft. My reason for this is quite simple. Microsoft is crap but unfortunately it is dominant. The draughting package Autocad is the same and I don't have to use that, fortunately. They insist on "upgrading" perfectly viable software or making it unusable on later versions. Examples of this are PictureIt which I still use and bugger 'em, and Access which with each successive "upgrade" loses really useful features. When you tackle them on this they insist that the features never existed in the first place. But I care not, I am quite happy using dos on occasion as well as various other OS. The only earlier one which caused me problems was 95 or was it 98? If it's not broken you don't fix it.
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