I used Chessmaster 5th and 10th ed intermittantly. Opinions i've seen on here range from Waitzkin being a money-seeker (duh) to it having value to get players to r1400 using just the standard course plan it lays out. Drills will help achieve some diligence perhaps achieve r1600.
Weaknesses:
It can't review your games like a person can
It's opening theory practice comes a little short of actual understanding, I prefer books and links to anotated games of such openings.
There's more endgames to study than what chessmaster makes available.
Match the masters seems like a big jump.
Strengths
Extensive archive of anotated games.
Ability to archive my chess.com games.
Can use the database to look for games played (not annotated though).
Plenty of drills and puzzles to keep the mind vigilant.
Really it's down to us at the end of the day to go through annotated games, review our own games and seek more experienced consultation.
I've just downloaded Chessmaster GM edition and fritz 13 and so far I've only played around with Chessmaster but I'm loving the academy so far, it really is good at explaining why a certain move is considered good and bad, teaching you to notice potention forks and skewers ect... but there is such a massive difference in spotting the fork when the program has just told you somewhere on the board is a dangerous fork waiting to happen, and spotting them in a live game with just a few seconds to make your move.
Who here started off with a low ELO on chess.com and then saw a dramatic rise in ELO on completion of the Chessmaster program? Or do you feel that the program makes no difference, the only way you got better was to just keep playing?