The way I see it, collaboration is the antithesis of winning. Players in a game can be focused in terminating the game by winning or by declaring once side as the loser. In collaboration, all players are focused intently in keeping the game going.
Wikipedia is indeed a finite game, but has embodied many traits of an infinite game. For example , there is WP:IAR: If a rule prevents you from improving or maintaining Wikipedia, ignore it., i.e. if a rule prevents the game to continue, ignore it. The challenge is, thought, as Wikipedia grows in importance, authority, and reach, its basic principles of collegial collaboration, civility, anybody can edit, free content, and neutral point of view (WP:FIVE) are being challenged by more traditional forces, which I would call routinization. This routinization is visible in the quite large body of policies, guidelines, manuals of style, etc. that has developed as well as the processes developed to keep the game going: Arbitration, Administrators, Page protection, Bans, Blocks etc.
As soon as these routinizing aspects begin consuming too many resources — and in Wikipedia the only resource is volunteer time (besides the $$ needed to run the servers and keep a small staff) — the purpose of the game begins to be lost: Rather than build new articles, improve new ones, expand the number of players, encourage participation, etc. the most experienced people and those with most time, tend to spend their wiki-time in areas that limit play. I am not arguing that these tasks are not needed; they are. Only that over time, the fundamental principles of Wikipedia get lost or constrained in such a manner that it impinges in these principles and may eventually lead to terminating play.
As a former Wikipedia editor that invested quite a bit of time in that area, I am aware of the dichotomy it presents and the challenges in bridging it.
Another challenge is when players try to bring about other games into Wikipedia than Wikpiedia’s own. Players try and transpose the games they have chosen to play IRL, into the Wikipedia project. That is why we have WP:BATTLE, the other side of WP:WRW. Just witness the ongoing political, scientific, religious, and other such disputes that have been developing over the last years (check WP:RFAR/C for a good sample), and the many efforts by the community to overcome these challenges. A notable point is that in almost every Wikipedia arbitration case (with some notable exceptions), the result is the imposition of restrictions to participate fully in the game … “in order to continue playing, you are now restricted from playing”, an obvious contradiction.
So, as long as there are editors that will do everything possible to keep the game going, and do that with such grace and diligence that does not result in restricting play, Wikipedia may have a chance. But if these editors that are intent in winning the game at the expense of keeping the playing going, become those that steer the project forward, then it may not. My opinion is that Wikipedia is at that cross-road.
The new Arbitration committee, which IMO has more diversity than ever before, as well as having people that I admire for the brilliance of their minds and the generosity of their hearts, may be the ones tasked to see this through, that is if they managed to bring the community around to support their efforts when exploring these challenges.
Per Carse, it boils down to choice If you have to play, you cannot play. It seems that those that want to win the game, are usually those that feel compelled to play it, and are those that play it too seriously for their own good. And those that want to keep the game going are usually those that edit with a smile on they face, enjoying the game, bringing new players to the game and expanding the possibility of play.