I'm sure any individual middle manager would give you a very reasonable explanation for any of these behaviors. If you're operating in a political environment and you don't play the game you're going to end up the sucker sooner or later. How do you fix the problem when you need to be part of it to have any leverage to fix it? The only thing you have power to do in that situation is behave ethically or unethically (depending on who's definition of unethical you're using of course).
I'd like to think that startups that grow enormously will prove over time that slow enterprise-y corporations are at a huge disadvantage and that will slowly make it's way into business schools. But part of the reason risk averse behavior takes hold is because the stakes get higher as you get larger. Today's spectacularly successful startups are tomorrow's enterprises unless they make a deliberate effort not to be.
The reality is that for your corporate/enterprise-fully-entrenched-fiefdom-building management person easily buying things or having someone read documentation and configure something is just not compatible with how they operate. They need net 30/60/90, sales drone wine, dine & golf, "is this in the Gartner Magic Quadrant?", a drawn out high-touch sales engagement and consultants they can blame.
Risk averse is the name of the game and it doesn't matter if it makes the business too slow to compete because a middle manager will never be held directly accountable for doing exactly what every other politics-first middle manager is doing. You want to sell to enterprises? Get in with the developers but be prepared to provide all of the above to the people actually making the purchasing decisions.