I recently bought "Chessmaster: Grandmaster Edition" and have been enjoying that. One of the main things I like about it (and one of the big reasons I was drawn to buying it) is the personalities that it provides to play against. There are many of them from extremely low (rated less than 100) all the way up through grandmaster personalities to the Chessmaster unleashed. Several of the personalities are based on real people. Most of those are at the grandmaster level, like Alekhine, Fischer, Morphy and many others. But there are also several characters based on Joshua Waitzkin at different stages of his development. Most of the characters are provided with pictures (the exceptions are the real grandmasters and I imagine it has to do with getting the rights to use the images which is of course not a problem for made up characters). These characters are also given different playing attributes. I find that these two things in combination give me a much more vivid experience than playing Hiarcs set to some specific elo rating. For instance, I have been playing two characters, one is Josh-age 6 rated 1200. He will play the Scandinavian defense most of the time. So, what I find is that the combination of the name, the photo, and the playing style get me more engaged in the battle. I have more of a sense of wanting to win. It's still not like playing real people, even online, but it's definitely nice for when I don't feel up to playing a real person.
The other major thing I like
about Chessmaster is that the wealth of very low rated personalities,
(there are many personalities rated under 1000). This means that my twin boys
who are 8 and don't seem to be prodigies can get a game where they have a
real chance at winning. One problem is that they can be a bit
competitive so if they play each-other, then feelings will often get
hurt at the end. Playing me isn't much fun as I am better than them. I
suppose I could try to play weaker moves but I think that would be
pretty frustrating for me, particularly when they would miss some simple
gifts I might offer them. Playing against the computer is good because
they don't mind losing to it, particularly because they can win a good
number of the games. I also think for them there is some sense that the
different personalities are engaging as well.
also comes with some tutorial material. I have tried out a little bit
of this but not delved deeply and it seems reasonably good. There's
also a database of professional games and an area geared to little kids
with cute rabbit pieces and stuff like that. I got it for $20 for the
download edition at amazon. Particularly considering the price of most
other serious (and note Chessmaster has beaten a grandmaster) chess playing software this seems to be a great deal.