I'd like to live in a world where companies like Jive, GitHub, Atlassian and Continuum Analytics could open source their core applications and collaborate openly, without it posing an existential threat to their business.
I'd like to think that software consumers were enlightened enough to realise that there's only so much that can be done with purely volunteer efforts. Seriously: there's lots of important stuff involved in doing software development really well that doesn't get done with only volunteers. That's why the MSDN docs for Windows APIs are so much better than what we can provide for Python on python.org, why the level of review, auditing and testing Red Hat can put into our products outstrips what upstream can muster, and why the overall road map for Python is so hazy it barely even exists (PEP 0 gives some guidance, particularly since I cleaned out a few entries from the "Open PEPs" section, but it's not a real road map).