Thinking about it, I actually would prefer a "public good" model: put a price on each chapter/part of the book and say "it would cost me x dollars to write this chapter". The moment you get a total of x dollars in contributions, write the chapter, then make it available for anyone to download. That way, _if_ the book gets written, we get maximum benefit to everyone. After all, once written, the marginal cost of copying the book is zero.
Any donations above the target could go towards future chapters, or to the writer, or to the FreeBSD foundation, etc.
"But people will just wait and free-ride then!" you may say. Yes, I know :). But maybe not. The key is that free-riding means waiting. If there are enough impatient people that wouldn't mind donating 5-50 bucks to a book that would help them _now_, this might work. So you want to make the book most useful to those impatient (but not cheap!) people, that do not have a lot of time on their hands to become experts in ZFS/networking/security/admin etc. My guess is that FreeNAS mini buyers are precisely that kind of audience.
By the way, does iXsystems have any data on the FreeNAS userbase? Or at least on the FreeNAS mini userbase? I ask because knowing the audience (their skills and time constraints, job and number of dependents or family size being good proxies, I guess) may help target such a book and also because it may help targeting people to write such docs (assuming people would be willing to contribute their expertise in writing, for a price).
Also, does anyone know the pricing / compensation models available in various publishers out there (O'Reilly, Manning, Leanpub, Pragmatic Bookshelf, InformIT, etc.). Do they offer anything along these lines? Anyway, paying an editor could be a "stretch goal"...
As far as keeping the book up-to-date, if one goes with the "public good" model, my suggestion would be to keep it in a public source control repository. GitHub is popular this days, so why not? And FreeNAS docs use reStructured Text... so why not?