Well, you can already quantify the difficulty of Boggle boards pretty well just by counting up all the points you can make on them (it's a small enough problem that you can do that pretty fast). I think the topology of the board is important enough (whether those I N and G blocks are next to each other or not makes a _big_ difference) that a simple histogram of letters isn't going to be sufficient.
You're right that with a Boggle board you could just count up the available Boggle points by finding all the possible words, but that might miss some aspects of how hard the words are for a human to find.
The game would end when all players had two few tiles to play.
In any case I've always wondered what the values of tiles should be if we were to use our current word list rather than the NY Times - thanks for this analysis. The blank is missing though, it would probably have a significantly negative value (-25 to -30?).
At the end of it all I'd rather keep the values what they are. Part of the beauty of Scrabble is the fact that there is chance. Despite the Z and the Q both being worth 10 points, one realizes pretty quickly how much worse the Q is.
It would be a service to us all.
There would be a lot of factors to consider that might make it hard to apply to re-valuing Scrabble, though:
1. Most Words With Friends play is casual, and casual players are likely to play very differently than competitive players.
2. The data would show you what words players play given the current scoring system, and wouldn't necessarily translate to another scoring system.
3. Words With Friends is a different game than Scrabble (different board layout, different bingo scoring, different number of tiles and different tile frequency).
4. Players end up playing the majority of the tiles they draw, so the frequency with which they play a letter may have a closer relationship to how many of the printed tiles have that letter than it is to the frequency of the letter in the corpus.
(You can, of course, play Scrabble with any dictionary but most serious folk I know use OSPD. I'd never even heard of ENABLE until Googling this question.)
Interesting analysis though.
A: 7 B: 2 C: 4 D: 3 E: 11 F: 1 G: 3 H: 2 I: 8 J: 1 K: 1 L: 5 M: 3 N: 6 O: 6 P: 3 Q: 1 R: 7 S: 9 T: 6 U: 3 V: 1 W: 1 X: 1 Y: 2 Z: 1
It makes a lot of sense to reduce the number of Ss for the sake of gameplay, and it seems like Butts redistributed those extra tiles amongst the vowels.
It's reasonable for someone with good reasoning or a large vocabulary to find it distasteful that they lose consistently simply because they haven't memorized the 1,000 most common moves. In chess, this is pretty much built into the mechanics of the game, but it's easy to fix in Scrabble with a simple house rule: Don't use bullshit words.
It's only part of the game if you let it be.
 I'll give an illustrative example. The official Scrabble dictionary lists "re" with the definition "the second tone of the diatonic musical scale". Just so for the other sounds of diatonic solfeggio that everyone knows: re, mi, fa, sol, la, and ti. All of these, according to Hasbro, are English words, with plurals.
We're all descriptivists here, that's fine. But did you ever wonder why there are only seven words for the diatonic scale, but actually twelve tones in an octave? Or why re, mi, and fa have different vowel sounds? The answer is that solfege has a way to verbalize accidentals (notes not in the key) or non-diatonic scales by modulating the vowel sound. A raised do is a di; a lowered re is a ra. So you can easily pronounce a chromatic scale beginning at do: do, di/ra, re, ri/me, mi, fa, fi/se, sol, si/le, la, li/te, ti, do. (The syllable used depends on the key.)
Go ahead, look up any of those accidental syllables in the dictionary. La and le: Both French articles, both solfeggio syllables. Only one is a Scrabble word. You can't say that's not stupid.
(Like another poster in this thread, I do also play friendly games with an open two-letter-word list, to level the playing field for people who don't care to memorize trivia.)
I'm not saying that the idea of a canonical word list doesn't make game-mechanical sense, just that it turns Scrabble from a word game into a list of symbols game in a way that seems stupid to me.
It's not meant to be more than an intuitive house rule to encourage people to play with "real" words.
Oddly, though Wikipedia deletes programming languages like Factor due to non-notability, editors get to go nuts on everything chess or Star Trek without recourse. If you want to know more about why things in chess are the way they are, Wikipedia is your pal.
If you want to start an argument, stop someone from castling through check.
Right off the bat, you need to pick a set of words that are allowed. Tournaments play, of course, allow a small set of those odd two letter words. However, both sides have to agree on a word set up front. it's perfectly reasonable to pick a dictionary that doesn't recognize "za" as a real word for pizza. However, i think if transfire really wants to use "fu", he'd have to resort to urban dictionary for the word list. That also admits za, so it's kind of a lose lose there.
It has really helped cut down on the number of games where we get stuck or frustrated because there's "nowhere to move", both by making more moves legal, and helping us keep the board configuration more compact, while at the same time eliminating what we see as trivia (what 2-letter words are legal) vs. "regular English" in the games we play.
'za' was added in OSPD4, which was published in June 2005: http://www.merriam-webster.com/info/pr/2005-scrabble-diction...
Michael suggests ordering some za in Season 2 Episode 13 (The Secret) which aired in January 2006.