Thanks Joe for the long post and for fixing my posting mistake! 
I just typed out a long post and got a Server / n application error when I tried to submit and lost the whole thing 
My fault - I know that when you use DNN's forums you need to copy the post to the clipboard before hitting the submit button because DNN's forums suck! Sorry, just had to vent.
Joe the main issue I have with your statements on contributions is the same as Rob's - there are no doorways to do so. IF you are relying on potential contributers to submit work unsolicited in hopes that the DNN Gods will be pleased and use it I think you may be disappointed. Who would want to invest hours on something that may not get used? That sounded smart-ass but it wasn't intended that way.
With regards to business valuations - if you are dealing with investors/bankers that are that out of date - direct them to read Wikinomics - if Procter & Gamble can rely on volunteers why not DNN or PowerDNN? If fact P&G type companies are severely limited on how much they can use collaboration so DNN has a leg up on even the largest companies.
Yes I'm sure that skin designers would want advertising on their skins that get included with the build. But DNN already does that now for certain sponsoship levels so what's the difference?
I want DNN corp to make money, I want the core team to make money, I want everybody to make money. So speaking of making money and sponsorships here is another idea:
Based on the information available to me I would say that all DNN members could be grouped into two groups - DIY newbs and developers. I would guess that the DIYer's are probably 60% of the users and of the 1000's of visitors to DNN.com we see everyday even higher. So why would you cut out 60% of your potential sponsors by making the entry level sponsorship package $250? If you were to make the entry level sponsorship package $60 ($10 to cover the cost of the DNN T-SHIRT) then you could take advantage of the new economy method of making a little off of a lot. i.e. If you got 1% of your 600,000 members to go for the entry level package that's $300k per year! If you changed the sponsor avatars you could turn them into a status symbol and drive sponsorship even higher. They need changed because they look too much alike - no differentation.
This thread has gotten me to look in areas of the website I normally don't. And I have seen several of the ideas I had are already here - just buried deep in the site. But many of them need updating or fixing. i.e. The TrainCert intro video built on DNN 3.0??? Or the demo area that is broken - at least it was broken when I tried it.