I don't know about Chessmaster, but if you want to find out how good you are against an engine, try playing with the free chess software Nagaskaki.
You can find it here: http://www.mayothi.com/nagaskaki.html
It was tested against other chess engines and found to have a rating of 2140 (source: http://www.computerchess.org.uk/ccrl/404/rating_list_pure_all.html).
If you can beat that then maybe you are above 2000.
You can also try Crafty, which has a rating of 2811 :)
It is available here: http://nightmarechess.com/crafty/. You can also adjust the strength on it as well.
Or, for something much easier you can try the tarrasch toy engine: http://www.triplehappy.com/. It has a rating of about 1400.
These are all free software and will give you a decent idea where you stand, if you don't believe chessmaster.
I recently got "Chessmaster Grandmaster Edition" and have played a few games in "ranked play" mode. In this mode it doesn't let you take back moves, or even save a game that's still in progress, which is a good thing I guess, because I have a habit of taking back bad moves against a computer if I can, because it is not as if a computer opponent "cares".
I've been playing the suggested opponent personalities (time control was Fischer 20/20). I've played the following personalities with the following alleged ratings so far:
• Seb - 1299
• Liz - 1495
• Marie - 1675
• Waldo - 1763
• Roxy - 2013
I beat the first 4 personalities, and it was a draw against "Roxy". I was up 2 pawns at the end (and then 1 pawn after I allowed one to be captured), but we both had queens, and she was able to perpetually check / force repeated positions, and the 3 repetition rule went into effect. Here's that game:
Now, I highly doubt that I could beat someone with a real USCF or FIDE 1763 rating (or even a 1675 rating), and I also doubt I could draw with a 2013 rated player. I've never played in a tournament and I've never played someone with a real ranking, but when I first got online in 2000, I played quite a bit of chess on Yahoo (usually Fischer 10/10 time control), and there my rating hovered around 1500, for whatever that's worth.
In any event, does anyone know what these Chessmaster personality ratings translate to in real life? They seem to be greatly inflated.