Like many books, it has chapters which correspond with a topic or set of related topics. Clearly this is to differentiate it from a blog, which has useless titles and possibly no topic. The author, Scott F. Andrews, used to write "Officers' Quarters" for WoW.com.
He starts out slow and obvious, talking about the creation of a guild. This was actually an excellent pair of chapters, since while much of it is obvious, it's the sort of obvious that we easily forget to remember. However, despite his ridiculous claim, "Fluffy Kitten Smile Time" is an excellent name for a PvP guild.
His analysis of player types and personalities was useful, but I didn't feel it was directly applicable; the analysis would help us to do our own, but his categories seemed to have a bit of overlap. The drama chapter is excellent, with strategies for dealing with and avoiding conflict. Loot drama is saved for the next chapter.
Possibly the most useful chapter is 6: Loot Distribution. It lays out common loot systems, and common exceptions. Even better, it includes complexity, officer burden, and mostly importantly: drama chances. If you're involved in planning a loot system, read this chapter.
I laughed a bit at the combination of PvP and RP into one chapter. If you're just glancing at it, you might be confused, or possibly offended if you only do one or the other and resent the implied "these are the other activities." The PvP section felt short. Honestly I can't recommend it the way I did the loot chapter. In contrast the RP section, at least to an outsider like me, felt like it broke down the different levels of immersion and how to help create a shared experience.
Similarly, the officer chapter is a mixed bag. The information is practical and useful, but the presentation felt strange. Yes, I realize that was incredibly vague. Okay who has heard of a Communications officer, Disciplinarian, or Drama Squasher? I've not been in a leadership position in a long time, so maybe I'm just out if it. They sound like strange roles. Who could possibly be friendly towards the officer whose only job is to tell you you're breaking rules? Drama Squasher seems like the kind of role that should never be assigned, that it would only make drama official, and make drama control seem artificial: "Oh look, here comes the squasher. Let's all pretend to be nice or the Disciplinarian will gkick us."
The chapter on maintaining morale is fun and filled with fun ideas. It suggests guild events like "Splat" and founding your own religion. How can you possibly go wrong? My only gripe is his failure to take the obvious next step: whoever wins the Splat competition is the prophet of the religion. Okay actually it's not just about morale, but all the stuff about not making your guild look like total assholes was a bit boring. This transitions well into real life, an unexciting but practical chapter about... real life: conflicts, problems, priorities, and meeting in that strange realm.
Overall I found The Guild Leader's Handbook to be helpful, easy to read, and at times entertaining (though at times not). While I don't think $25 is an unreasonable price, and it's certainly a better buy than a pony, unless you're serious about being an officer or GM (many words were devoted to explaining why GM is a bad title) it's perhaps a bit much to spend. But perhaps that's stating the obvious, just as you'd not buy the novels (it's better written) if you don't care much about lore.
People who like this sort of thing will find this the sort of thing they like.-Abraham Lincoln