Re: the NSX glitch not a sign of troubles in engineering
Nate, you seem to be misunderstanding Agile there. Break early, break often is there to improve stability by stressing things to show the cracks. Agile and DevOps also include "test thoroughly" which is often missed - unit testing catches many issues before release. Stability by obscurity (i.e. not looking for broken things) is akin to security by obscurity - it simply doesn't work.
The old adage of being a few versions behind has been demonstrated as ineffective over and over again. Certainly no sane admin will roll into production third party software on release day other than security patches, but whether you install today or in 3 months time the bugs will still be there. The bugs are what get fixed in the next version so the only way to get around them is to install that newer version. Waiting until there's a release you're comfortable with is the reason there is still so much NT4, 2000 and 2003 running in the industry!
Real stability is gained from good practices. VMware seem to fail often here, but others such as Amazon (AWS) show that you can move fast while remaining stable and trustworthy. Through the use of careful roll outs of new software and features they are able to constantly change and update while not affecting the platform.
I wouldn't consider a 4 month release cycle as particularly agile (or Agile, for that matter). It missed the entire point of smaller releases and shorter feedback loops. 2 weeks is considered the norm, while those who have perfected the practice release multiple times a day (sometimes thousands of times a day).