What makes a good Rulebook?

An interesting post with lots of different ideas to dig into, I'm just going to hit a few that struck me as I read.

1) How important is a good rulebook? Well, as you point out there are popular games that have lousy rulebooks and most people learn from another player. However, I would say that having a clear set of rules can only help you. While you may be able to start a chain of teaching at a gaming convention, if the rules are hard to follow or confusing you'll be turning off your customers. The games that are popular with bad rules are only half the story, we don't know how many cool games never really got off the ground because the rules were poorly written. If you are presenting this to a publisher, good rules will certainly make a better impression and the easier the game is to pick up and play the happier your players will be.
1a) Aesthetics - visual and textual. Summary - these are things that add to the overall value and appeal of your game, neither is likely to make or break it alone, but they can both help create a positive image/experience.
Personally, I really don't care about artwork (I had blank white walls before I got married), but many people do. I have a friend who bought new Dominion cards with fancy new pictures for the copper and gold and people like to buy things simply because they look beautiful to them (personally, I'd rather buy a new game, but that's just me). However, I think your rulebook art is less important than the artwork for your game. In terms of flavor text, I think it follows the same pattern. I find the Galaxy Trucker rulebook hilarious and have recommended that people who were taught the rules read it just for the humor value, but I wouldn't suggest buying it for just that reason.

2) I tend to think quick start information is handy because most* people do not want to read for an hour before playing a new game. A quick start set of rules and explanations backed by a good detailed explanation later on is a nice, but not necessary feature that helps get people drawn in and invested in your game. Rivals of Catan, a 2player card game has a base deck and suggests a short game using that to play your first game so you don't get overwhelmed with all of the possibly combinations right off the bat.

3) If you refer to an interacting mechanic that you haven't explained yet, instead of getting sidetracked, just insert a reference to the page or section so that the reader knows they interact and can skip forward if they really want to. Presumably you are introducing the first mechanic before it because it makes more sense that way and most people will just follow along with your logic, but the reference will help satisfy the more curious gamer and help when people are reading through the second time to catch how things interact.

4) You could also do a basic rulebook and then have a player almanac as two separate items (or sections) to separate the basic questions vs the in depth explanations. Based on your description of the length, I'd want an almanac, but that's a lot of work, so it depends on how much you want to help out your players . . . more is usually better, but the return on time invested might not be worth it unless there is some automated way of generating it.

Good luck with the final stages of your game!

I love this post, it has way more than I can respond to at the moment.

I will say what is probably the obvious, but a glossary and table of contents for a lengthy rulebook is a must in my mind. Games that can implement keywords should almost certainly do it on any difficulty scale, it makes reference much easier and players can typically memorize the rules better in digestible clumps as with keywords.

Taking into account different learning styles is pretty key also, pictures and words that "say" the same thing will be helpful, even appealing to the kinesthetic in us all by integrating set-up (the touching and maneuvering of the board/pieces) in with the rules whenever possible.

If something doesn't appeal to a player they skim to the thing that does.

As for playtesting, my very small company is excited about playtesting and reviewing indie games. I will message you.

Galaxy's Edge springs to mind. I felt like I had a firm grasp of everything that was going on after one read, and it was not a chore to read it.

The balance should lean towards whatever your target audience is. If it's a family game, it needs to be expressed simply, with little or no jargon. If it's a gamer's game, the jargon will help them grok it faster.

Start with the simple explanation ("Trample damage deals damage to the blocking creatures first, then any extra damage is dealt to the defending player"), Then give the thorough explanation. If you're going to have "quick start" rules, these would be in separate places. If you're not, these would usually be together, one after the other.

This would be something best answered by the playtests. When you do observed blind playtests, pay attention to the small hang-ups. Did they have to consult with others at the table to make sure they were understanding what was written? Did they stumble and "um... i think..." over particular parts? If you can't solve this with re-wording the basic rules, then you probably need an example.

I like this for longer rules, so that when I have to skim for the right info, i can skim the sidebar. In shorter rules, sidebars are usually better for gameplay hints and fluff, so that they're not slowing down the initial run-through of the rules (i.e. maximize the advantage of having a potentially short rule set).

Right hand side, usually. Important info starts on the left/top, summary/other things on the right. Look at your standard webpage, then google heat maps for eye movements of people when they're browsing. Similar concept. The lack of symmetry won't be noticed when actually reading, and having a consistent place for your eyes to go is more important (usually).

Very often, you can re-arrange the order of explanation so that mechanical terminology won't overlap unfavorably. For example (sort of), Dungeon Lords essentially opens up by explaining combat, THEN starts in on order of play. If you absolutely can't find a way to arrange this, try to make the mechanic terminology be words that make sense contextually, or that can be explained briefly. For example: "...then draw 2 cards and keep 1 from the deck (following the same rules as 'Accessing The Database', below)" would give people the basics, maintain the flow of the explanation, but lets them know that there may be more to the action than simply "draw 2, keep 1".

Yes, you absolutely can (and usually should) oversimplify the initial goal statement. "In fair Verona where we lay our scene...", not "in the sub-county of Verona, governed by duke something, population of 12,597, average taxes of 3.2%, unemployment rate of 18%, poverty level 25 gold crowns per season, council member names are...". Enough information to get you moving into the turn structure. More thorough victory conditions can be handled later.

The answers the previous poster gave were very good.

a) nice if easy to accomplish, but not necessary, generally.
b) Plain white background looks cheap in MOST rulebooks, even on shiny paper. I would consider very basic and unobtrusive texture or art standard.
c) Nice if you've got the space and/or art budget for it.

I will add that quick lines of fluff or small pictures are best used when they add to the thematic mnemonics associated with particular rules. Don't put the picture of the gunner next to the rules for melee, put him next to the rules for shooting. If a mechanic represents haggling with NPC's/the game system, but doesn't state that explicitly, a quick blurb or a picture of someone haggling with a merchant is both functional AND thematic.

Depends on the target audience. Puerto Rico players? Just a tiny bit of fluff/history, get to the rules ASAP; The box cover and description on the back handles most of the theme for you. Twilight Imperium 3? ART! FLUFF! THEME! MORE! Family games? somewhere in between.

I think this is mostly answered above- examples when needed based on playtest results. Glossary/Index for longer rules (as prior poster mentioned). Strategy tips are best used to make sure a key concept is not overlooked, because often only the player who reads the rules will see them.

I think one of the best things I can say about illustration examples- do your best to make sure people can play the game with TEXT ONLY (that's what blind testing is great for). Then, once you feel the rulebook can convey everything is necessary, you can add illustrative pictures to make it EASIER. But don't remove the text, expecting the players to use the explanatory pictures, because people will gloss over things you wouldn't expect them to. Giant picture, "IMPORTANT!" in big bold red text with arrows pointing at it, and they'll still flip back and forth through the rules, looking for something they'll later claim "just wasn't there".

Will it be the singular thing that MAKES your game a hit? probably not by itself. It is one of many many factors that can contribute to a good experience, and people actively wanting to share that experience. However if the rulebook is BAD enough, it CAN be the thing that prevents your game from being a hit. I recommend not aiming at the middle ground. In any undertaking, the last step is as important as the first.

A good rulebook takes time, but not necessarily additional money outlay. On that basis alone, people should work harder on them than they do. For smaller companies or newer designers especially, they often don't have a "process" to make sure the rulebook is up to snuff, so the rate of bad is significantly increased. Desire to make a good rulebook is more a matter of work ethic, an "I want to make sure MY product is GREAT!", which should be the mentality associated with the whole process. But patience in the process is also hard to come by for lots of people, particularly if they think the game mechanics are finished.

Just to answer one of your questions: I really like the Axis & Allies rule book(s)

Discs! That's old school. Why not just a QR code to a YouTube video, of if you really want to go nuts, a how-to-play mini-site?

The reference vs sequence of play dichotomy is interesting. I can't stand reference rulebooks, but I do want the sequence rulebooks to be more reference-friendly, whether through an index, or good summaries and clear marking of exceptions or unusual rules. I wish someone would write sequence-style rulebooks for games like Hannibal or Twilight Struggle.

An index helps SoP a lot, as a reference tool. I write SoP now because it's expected, but I include at the front a detailed table of contents, which helps a lot.

If you are talking about it, there should be a picture of it.
There should be pictures throughout your rulebook. In fact, you really shouldn't go more than a couple of paragraphs without a picture - either a picture of the component you are discussing, or a picture of several components working together. People appreciate being able to reference them while they read.

Second choice: More examples. State a rule, then use the rule in an example.