"But I still want to ask: Are philosophers happy with this situation? So little time and effort is spent trying to bridge the divide - or even understand it - one would think they must be. And that strikes me as simply amazing.  After all, we are talking about philosophers, not finches."

Well, to continue the finch metaphor just a bit further, once another group has deviated so far as to become a different species, the urge to (ahem) breed with them subsides.  If the other side "isn't really doing philosophy" or is engaged in "muddle-headed obscurantism" or "tedious dry logic-chopping," then why put in the effort to learn their lingo?  It's a great deal of work and, from the outside, it looks unpromising; that's part of what it means to be on the outside.  So I think many philosophers are unhappy with the fact that a bunch of imposters are soiling the good name of philosophy, but are quite happy knowing nothing about them.  I have made up my mind about Ayn Rand, for example, and have no interest in spending a lot of time perusing the secondary literature on her to make sure that I'm right in dismissing her.  It's too much work to spend on the chance, which I have estimated as negligible, that I may be wrong.  The fact that, without sufficient background, the other side looks deeply unappealing then gets reinforced by all the sociological factors: when you're looking for a dissertation chair, a job, tenure, invitations to speak, etc., do you want those in charge to scoff at your interests?  Why bother putting your reputation at risk when it already takes more time than your natural lifetime to master and keep up with the literature of your chosen area?