There was some trouble with the .ini file, that is why the book was not being used. I have no idea if this is a general problem or if it only occurs when using Winboard to play on ICS servers. Anyway I disabled the feature so the opening book can be used. I also switched to a larger book, compiled from a number of pgn-files. I have not tested it that much but hopefully it should help a bit.
The crashing upon game completion was of course the all existent memory overflow problem with Java, I had simply forgotten the -Xmx1024M flag in the Winboard batch file.
And finally I added kibitzes at the last ply of the search, and a note if the move is a book move or not.
So one hour to go and I am ready to see Mediocre getting lucky! :)