I, for one, never thought that dot-Net had a bad design. I certainly would not call it “worst of all,” except in the good-humored jest that I recently used in reference to Java. The dot-Net framework is a very good design for the “single-vendor centric environment that is Microsoft Windows.” There are millions of deployed copies of just such an environment. Its biggest problem is, admittedly, a conscious design decision: it is made for Windows, for Internet Explorer, and it depends quite heavily upon client-side functionality that is also built-in to Windows (and/or to the “Silverlight®” plug-in which Microsoft provides). Therefore, if you are deploying within a company’s internal network, you can do amazing things ... but the moment you wish to go out, you have a problem.
And where, exactly, do people (within the company ...) “wish to go out?” You guessed it ... mobile devices. Whether they like it or not, Microsoft lost that battle. So, to a lesser extent, did Blackberry. Windows-CE et al is simply not on the radar at all. Microsoft never will own that environment, nor will they own the deployment avenues leading to it. Never. “Game Over.™” What the Executive Vice-President is carrying in his jacket pocket might be an iPhone, but it is just as likely to be an Android-driven device that does essentially the same thing for hundreds of dollars less. Your challenge now happens to be an extremely big one: to bring the functionality of that internal application securely to the EVP’s jacket pocket, and to make it robust and reliable, without access to the dollars needed to re-do the whole thing in a sensible language, such as Perl. ;-)
But we can’t blame that on dot-Net, nor should we count-out Microsoft’s very capable development team (which has produced many miracles in the past). They simply based their system on the assumption that they could control both the server and the client side ... and, in many still-existing cases, they can. It wasn’t a “flawed” design. In many ways, IMHO, it was a brilliant one. (And is the game really “over?” Heh, in this business, “never say ‘never.’”)