Hi, sympathetic outsider reporting here:

For me personally, as a member of the volunteer focus group, the reasons that plan 9 is such a pain are the same reasons I'm drawn to it:

  1. Plan 9 is a network OS. The downside is that a single, disconnected plan 9 workstation is a pain in the ass to use, and is crippled by design (I think). Unfortunately, very few of the kind of tinkerers who would enjoy it have enough spare hardware to build something that really shows off the strengths of the system. I think the xen port work is the best fix for this, since it allows me to build a network using a minimal hardware footprint (I haven't tried).
  2. The interfaces are baffling.  As Master Shake said, "It's too advanced to be compatible". Not just rio; I mean adding a user to a system, logging in under a different account by rebooting, mounting devices as filesystems, making configuration changes, everything is different. I don't think anything makes sense until you understand the entire system, top to bottom. It's a difficult investment to make. I appreciate that this is not your problem.
I think that I understand the picture that the forefathers had in mind when developing the system, it's just that it's very difficult to implement an infrastructure that shows the benefits of the plan 9 approach. And when you finally do, It's not clear that you've got something better, because there's nothing you can do after building it that you couldn't do before. Of course, enthusiasts do not represent a significant source of government funding, and are thus unlikely to have significant input to the roadmap. I'm just sayin', is all.

Rob