I am planing to do the same and have done some research on it. Wasn''t a real succsess. Found lots of advise on storm taktiks and what your boat should be able to take. Also lots of stuff about sailing experiance to do it but no real information rounding the horn it self. It''s well knowen what to deal with doing it, so if you have a ocean going boat and the confidence to do it plan the trip as any other one. Guess the best help are the official sailing directions of this area. I just ordered the official sailing directions from UK.
However it''s been done in both ways. The "easier" way is from west to east cause of the main wind directions - westerlys. The best time doing it is some time december january.