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Do you like chocolate or vanilla ice cream?
The tools are similar in terms of capabilities. If you are a Microsoft shop then choosing Silverlight makes sense. If you already know Flex then stick with it.
Both Silverlight and Flex are mature and powerful technologies. Neither of them will have significant investments in new capabilities because the industry is focused on HTML5/JavaScript.
Browser plugins are not currently in vogue. I find it fascinating how the industry goes in circles. For example, many years ago a lot of work went into virtual machines and distributed computing. That then faded away but it is back in vogue now. I think that web programming will have to evolve to something at a higher level of abstraction than HTML, CSS, and JavaScript. I call this devolution.
My 2cents as a consumer (not an Esri employee)... My my iPad doesnt have Flex or Silverlight support. It's really annoying when I visit a site which tells me to install Flash and I can't.
Who are you building apps for? How will they consume them? Just other questions to consider.
survey says......html5 and javascript
Hi Timothy,
FYI, we've integrated HTML5 technology into our JavaScript API, where appropriate. Please see the recent UC 2013 Q&A,
Can I develop web and mobile applications with ArcGIS and HTML5 now?
And this article might be helpful,
Creating Custom Web Mapping Applications without Programming
Hope this helps,