> Usually it's a win win, unless you value keeping control (which can be quite valuable)

My experience is that it's usually overvalued. An external, focused company will usually do a better job than an internal project. It's emotionally hard to give up control, but successful companies tend to focus on a few things, do them really well (areas of competitive advantage), and outsource everything else.

A best-of-breed external solution almost always beats an in-house solution.

I'd just never do something like this with Oracle. Their business model seems to consist of locking companies in, and then milking them.