"And I know there's a lot of MS hate from IT people, and sure, I hear you, they could do a lot more to make it better for all you tech wizards that know networking like the back of your hand. It's probably that which is clouding your judgment of their system. To a non-programmer, non-tech guy who thinks CLI is some small government agency and not common language infrastructure or command line interface, MS's stuff is gosh darn fantastic."
Your post implies that non-tech guys' opinions are the only ones that matter. When you need a tech guy, and they can't/won't help you because you have chosen the option that nobody can easily fix, you better have honed your vendor arse-kissing skills in advance because most vendors aren't that helpful unless you give them lots of money first and 90% of the market share isn't going to pay a vendor (much, if at all) for tech support. Knowing networking well does not cloud one's judgement of the system; being technically knowledgable allows one to see features and flaws that the less knowledgable cannot; being knowledgable only "clouds" judgement if your goal is to be wrong.
But nobody should believe that a company that has for decades made tons of money by selling units of something that has no incremental cost of production, (copies of software or licenses to use them,) and which is publicly traded and whose investors expect it to do more of the same, will suddenly embrace a project that promises no direct revenues and which will compete with their existing product.
One of the ways you can tell that MS doesn't understand open source is that they are pushing Mono. There is a reason that Mono has been around for more than 10 years without gaining any real traction. It is a clone of
"Pulling JVM into the equation not really helps either, cause the consequent question would be: Do you trust Oracle? Or Google, for that matter if you count Dalvik in."
There is an open JVM. There is not a fully open CLR or a fully open clone of the CLR. So no, I don't trust Oracle, or Google, or IBM, (you forgot IBM's JVM,) but that doesn't really matter. Nobody who cares about their software stack being maximally open should be super-enthused about Mono.