Reverse compatibility
With apologies to Emerson... "A foolish devotion to reverse compatibility is the hobgoblin of little minded companies."
I read an excellent essay on the perils of attempting to maintain reverse compatibility at all costs. Of course Microsoft's motivation for using this approach was/is to control market share and has in fact worked very well for them.
Yet this strategy also acts as a self limiting aspect of monopolistic entities, and while it's a little early to be predicting the demise of Microsoft, we can certainly identify this as an opportunity for open source to make significant gains in the market.

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