Automatically annotating the beginning of my games

Question

I play chess online and use an engine to review the game afterwards. This works well when I get out of the opening, but under my current configuration (Raptor GUI running StockFish) I don't get great insight into the beginning of my games. Instead of using the automatic annotation I end up stepping through the first couple moves using a free online openings guide. There are two drawbacks to my current system:

1. Manually reentering my moves through a the web interface is a little painful
2. I could use a larger opening book and more detailed comments

Is there a tool (free or commercial) that will provide this? Bonus points if it runs under OS X.

I've looked at the offerings from another question on annotation, one that's not focused on the opening. It looks to me like Tarrasch will tell me what the book moves are, but not tell me much about them, and Arena does something with opening books, but I can't tell what. These are PC applications so I'm basing my comments only on the websites.

Answer 1

As far as I know, all the tools available today offer an opening book (tree) that has to be traversed manually by clicking yourself forwards and backwards in the book. To evaluate the position at every point of the opening, you can have an engine running and combine this with the statistics that are included in the opening book for white win / draw / black win. Relatively recently, Chessbase Online entered the stage. Let's not forget about Chess dot com and Chess 365 who also offer online books. So instead of having a software installed on your computer, you can use these online services to check and evaluate your openings.

Additionally, you could consider posting opening related questions here on Chess SE and get some valuable insights...!

Answer 2

The best move in opening positions is often very subjective. Player comfort with and knowledge of the position is much more important than an objective evaluation or database statistics. Databases can inform you of what has been played before and how it has worked out for other players, but not what you would do with such a position. Except for tactical mistakes, a computer evaluation is mostly worthless, because it provides no understanding beyond the evaluation.

Good opening books are the best resource.

Consider the difference between the statistically equal first moves for white. The choice between e2-e4, d2-d4, c2-c4, and Ng1-f3 is subjective. If the player has good knowledge and comfort with the postions, b2-b3, f2-f4, g2-g3, and even b2-b4 are reasonable choices. These latter are what I call "objectively not the best, but not bad moves". Opening positions are full of such moves. After 1.e4 d6 2.d4 Nf6, 3.Bd3 is a good example of such a move. 3.Nc3 is objectively the best, but since very few books on Pirc or Philidor cover this move, you can gain an advantage of knowledge by using it.

By the time club players reach move 10, they or their opponent are likely to have played one of these "not bad moves" and drifted into unknown or rarely played lines. Understanding the ideas behind the placement of pieces, general plans, and common tactics of the opening you are playing are more important than what has been played before.

Good opening books provide knowledge of positions and reasons behind evaluations. What is a good opening book depends on the skill level of the player. I generally find that the Starting Out series or the Move by Move series are the best for club players.