I would term myself in one sense the third generation of wikimedians. I did not come from Nupedia, or very soon after it, nor did I come in the great inundation of slashdottings, but I really came to specifically wikipedia when it had real useful content, and was indeed directed there by a link into an article, to settle a question.
It would be easier to list what contributions I am most embarrassed by, but I'll try to answer your question nevertheless. Unsurprisingly I feel I was able to bootstrap coverage of subjects to do with Finnish culture in terms of articles on wikipedia. In the early days of my involvement (2003-2004 or thereabout), I did a lot of new pages patrolling, and participated widely in discussions and developement and even initiation of policies that have become central to the way wikipedia today operates, and to the extent that my contribution was constructive, I suppose it is fair for me to feel some small quiet pride, deep in my heart. I am not really much of a person to brag about specifics.
I honestly think the best Board of Trustees is the Board of Trustees that does the least. But a Board of Trustees that will not shirk from doing that which is necessary. If we consider Wikimedia as a boat, the ideal configuration of it's functions would have the staff be the crew, with Sue Gardner as the First Mate, the Board of Trustees should be the Captain, and the Advisory Committee should perform the pilotage.
I would bring depth of representation from languages that aren't world languages. Currently the board has some representation from smaller languages, but large languages still are strongly over-represented in it's make-up. In the foreseeable future the content in the 10 largest languages will be eclipsed by the amount of content in the rest. But the ratio in the membership of the Board of Trustees remains very different, to put it mildly.
In terms of my personal characteristics, I am of a philosophical bent; tending to think before I speak when dealing with issues of significance, but when I do speak; I rarely will mince my words, nor call a "spade" a "flatbladed digging tool". Though I do think the thoughtful aspect is well represented on the current board, a little more plain speaking once in a while (even if hopefully it should be rarely needed) is something that I might reasonably contribute.
Apart from translation of content between languages and the developement of tools to facilitate that, one key area is to explore comprehensively what new possibilities are enabled by new abilities to use media other than text, primarily by projects like wikinews and wikiversity, but others as well.
In terms of stewardship of the Foundations assets, this is really the time to prepare for coming "lean years", and that is a strategic imperative. It has been continually spoken about, but this is the time to really make sustainability not just ensured by prudent spending decisions (as it fortunately has been), but set in stone by setting aside solid and reliable reserves for the coming years. Personally I think doing so will make us look more established and bring in more financial support as a result, not less. I imagine that should we set up an endowment, there are a significant portion of donors who would like to direct their donation there.
As noted above, it lacks an endowment. And translations of content aren't co-ordinated as indepth or done as systematically as with the proper tools, they might be.
I can't think of anything really that the Foundation is currently doing that is clearly and unambiguously harmful. There are areas where its activities will have to be scrutinized very actively, because there are real risks in acting in those areas, but I have every faith in the staff that directed by the Board of Trustees in the right way, they will continue to avert any such risks inherent in being a trail-blazer on the World Wide Web. (to remove all doubt, these risks primarily have to do with file formats, licencing and terms of service)
To embellish the reply I gave above stating that the Board of Trustees should do as little as possible; the way I see the issue of governance of this creature, is well illustrated by the story of the millipede. As long as the millipede lets its limbs do their thing, it progresses fine. But once it starts getting too involved in central introspection of what precise muscle twitches each leg in turn has to operate for the whole ensemblage to produce motion, things just unravel. The head of the millipede is well advised to observe its surroundings and make decisions on where to find food to provide energy for all its many limbs.
So in my view the board should support all activities that progress the Mission in the right direction, but leave the details of particular operation as low down to the ground level as possible.
Now not all matters can be done at a localized level. But my personal view is hard and fast centrally directed regulation is something that should be very stringently limited to those matters where it is nigh inescapable. A completely different issue is that I would very strongly support (if there was the internal impetus and willingess for it) the Advisory Committee developing into an active voice, putting into words in a centralized fashion the ideas it recieves from the community and other organs of the foundation, and refines into well crafted recommendations, whose wide application would derive from the inherent soundess of the consideration that had borne them. Long term there has to be some voice that has an authority not deriving from artificial constucts such as votes, but purely from the wisdom, experience and soundness of the consideration their views embody.
It is very emphatically not a matter of "sorts of partnership". It is all about setting red lines, and never crossing them. Wikimedia doesn't have to "chase" partners, nor compromise. That is just not realistically what we are about anymore. If other actors approach us and are willing to admit that our mission statement has merit and cannot be overridden or finessed in any way, that is fine, and we should help them support the things our mission statement is there to advance. I think that says pretty much everything I have to say on the matter. If there is something unclear in the above, please ask for clarification.
I think it is essential that initial steps are taken to create an endowment to act as an officially assigned safety cushion for the coming lean years. But equally the establishment of that endowment shouldn't be overly aggressively approached; it is never wise to bind the kine of oxen that plow. WMF is still in a growth spurt phase, and it should be fed resources accordingly, to not stunt it prematurely. Time enough to settle down later. But definitely the first steps towards and endowment need to be taken.
I am glad you asked this question, as it is one of the most central issues in this current campaign, with the method of choosing chapter nominated members of the Board of Trustees still not settled for good.
There are a few problematic aspects of chapters coverage of the whole of humanity. First of all it is clear that chapters will not in any foreseeable future cover the whole of humanity. That is a very significant factor to consider. How will we ensure that people who have no chapter to realistically represent them, will not be disapportioned of their legitimate weight of consideration Foundation-wide?
Secondly there is the issue of what places do deserve only one single national chapter, and which localities deserve many local chapters that are not considered in any way inferior to national chapters.
Thirdly we have the issue of which chapters that cover a very large ground, are still considered mere sub-chapters, purely by virtue of having a national chapter above them. Or whether such chapters (like the New York chapter etc.) should have a full force of a chapter that is usually only given to a national chapter.
Fourthly there is the issue of cross-border chapters like a prospective Catalan chapter, or I could imagine in the future a chapter in the Saami cultural area near to where I personally reside.
Make no mistake, these decisions are hard and even more complex than I have outlined above. I have to confess I have no hard position on these issues, but if there is significant discussion on these, I will participate with all the wisdom I have to offer, such as it is.
If the Advisory Board could be fashioned into a "Voice of Collective Institutional Memory & Wisdom", that would be awesome. We need a real philosophical sounding board and place where people who have "seen the elephant" can mull things over and give genuinely thoughtful and well balanced commentary and input into peoples perception of things as they progress crosswiki. I confess I suggested several years ago a Wikia project to collect all the alumni of wikipedia editors who had a sizeable track record of commitment and longevity in editing wikipedia, but for reasons that aren't quite clear, that didn't happen.
In terms of expertise on the Advisory Board not represented, I can think of two names in particular. Personally I think it is a shame that Sunir Shah (of Meatball Wiki fame) is not currently on it, for whatever reason. Also, a person who (even though Jimbo with his libertarian roots might well deny it) embodies many of the core working principles of wikimedia, in my view is Jurgen Habermas, and if he ever thought it tenable, having him join the advisory board would not in my view be a loss.
To address the last question first, (a trick I have learned well, and found quite useful) I consider myself a kind of a "Man For All Seasons" and will definitely adjust my attitude according to the times.
The first time I ran, the Foundation was pretty much just so much vapour, searching for a form to make it flesh. While I wasn't actually chosen to serve on the Board of Trustees that time, nearly all of the suggestions for the comportment of the Foundations structure that I proposed, were followed. Which is pretty nice.
"... has changed ... community or yourself ... expect a different outcome?" I actually have an abysmal predictor of the outcomes of these elections, so mainly I expect that to continue, and my predictions to not come to pass this time either. The main changes to myself are likely to note that I am now fully qualified to wear a grey/silver sided velvet cap with white top, black laquered flap and long gray/silver tassel mounted up top on the center of the cap, as graduated students of the mercantile arts have been from fin de siécle onwards, in my country. Having completed my qualification from the program of Library and Information sciences (how you consider Library and Information sciences as part of the mercantile and corporate governmental arts is not something I fully understand either).
As to the community, I would hope that it would have a heightened sense today of how strongly skewed the current board is in terms of languages represented, and how vital it is that there is representation on the board from people who aren't co-opted too deeply into the labyrinthe of internal mailing lists, committees and chapters. (And yes, despite being on the board of directors in a chapter about to be borne, I am still not yet quite co-opted to even that chapter as a bureaucratic entity :-)