Welcome to the fire&motion effect[1]. You now have three problems.<p>First, by chasing what some <i>other</i> people think is sexy technology, as opposed to going with what allows you do Get The Job Done, and quick.<p>Second, your misunderstanding on what the markets care (which is, well, marketing for the most part), and don't care about (eg your technological stack). None of these the things outlined in your post will make any difference whatsoever on your ability to chase lucrative market opportunities.<p>Third. Despite what some people here might write, "Hacking" -fiddling with technologies, and gaining a deep insight into them- is completely technological agnostics. You can be a hacker, even in VB.NET; it just happens, that some of these technologies has a better "average community member insight" factor, than others.<p>Thus, your question really boils down to something more fundamental: are you into "hacking" for the tech, or for the people? In the former case, it doesn't really matter whether you'll use MS, or Python, or what the state of the current MS devtools are -just that you gain a deep understanding of them.<p>In the later case, you should put your investment into <i>people</i> -the ones you'd want to connect with, anyway- and let the appropriate tech emerge from it naturally.<p>[1] <a href="http://www.joelonsoftware.com/articles/fog0000000339.html" rel="nofollow">http://www.joelonsoftware.com/articles/fog0000000339.html</a>