Debian is in an interesting position. One of the most valuable lessons I learnt from my time owning a business is that in companies, your lawyers and accountants always give you conservative advice. In a company, it is the job of senior management to weigh legal (or whatever) risk against the expected returns in profit or number of customers, etc. In Debian, we have plenty of good legal opinions but we have no profit motive to pull us back the other way. It is, therefore, completely understandable that Debian should drift slowly toward a more conservative approach to legal matters.
Now I'm in FOSS for the freedom part—don't ever think otherwise—but I am concerned that Debian's “profit motive” (the benefit to our users) is being slowly eroded. The constitution says our first priority is the needs of our users and the free software community and I am not convinced that an extreme position on “freeness” is the best way of furthering that community.
A way that I can see to counter this is to have some sort “legal committee”, which is granted the task of determining what should be in main—not simply if something is DFSG-free, but also making a subjective call in “grey area” cases like fonts, particular documentation and firmware. Perhaps they could take their cues from what the various distributions that do have a profit motive have decided is an “acceptable risk”. We can turn “no-profit motive” into a feature by realising that vendors are much less likely to actually launch legal proceedings against Debian or its users, due to the PR damage that would cause. Assuming we respond to any vendors' complaints in good faith, I believe Debian can make a few mistakes here and suffer no ill consequences.
Until this is done, there will always be room for the Ubuntus (ie: Debian with the reasonable bits put back in) and this is a shame. I would rather be associated with a distribution the community can all be proud of, rather than merely a good framework for one.
OK, so SPI has problems. It's not at all clear to me why Debian would manage our assets any better ourselves. If SPI decides it wants to be more than a bank account and legal entity (eg, SPI becoming a political lobby group) then we will have to reevaluate that of course.
Besides which, I live in Australia and any organisation's 501(c)(3) status has no real meaning outside US. An interesting idea that would benefit users is to create non-profit Debian entities in many countries, managed centrally by Debian. SPI could of course remain as the US-specific piece, but I'm not sure I would be comfortable with SPI becoming “Debian International” themselves. Some countries have part of this already in place but a lot more could be done for non-US donors.
I am concerned that Debian's mailing lists are getting in the way of actually getting things done. We could implement list moderation using a number of different techniques. I think it is a discussion we need to have and something we should experiment with.
Often, I have met someone in person and been surprised by the difference in their demeanour and the ease of communication, compared with previous email exchanges. I think the software and bandwidth is now available for Debian to promote VoIP as a useful means of communication. It would be a simple matter to add SIP/IAX/H.323 information to db.debian.org, publish a few HOWTOs and encourage developers to take disagreements and high-turnover discussions “offline”. Putting voices and faces to names would hopefully have some good social effects too.