The Bay 12 Mafioso Chess Club?
I'd certainly
in for that. Much more interesting than the iSketch craze that took you guys over recently. It'd be as easy as people creating accounts where wuba and I played, friending each other and finding games there (maybe posting in the discussion topic when you'll be around). If more interest is sparked, we could set up tourneys and post results lists and whatnot.
If WUBA wins, can I be the next challenger?
I'm sure he (or I) would be glad to play a few games, but I don't think either of us will risk the soul/title thing that soon. The betting thing is interesting though; if you wish to issue a challenge, and both parties find the bet balanced, it should be doable.
As far as chess software, the long list of ChessMaster titles is pretty good, has plenty of different levels/personalities to play against, has puzzles, openings, book, endings, tutorials and so on, and old versions should be found on the discount bins of any store (or on abandonware sites). The version from 10 years ago should be less than five bucks, and it's certainly good enough. From the Free Software side, GNU-chess, phalanx, and glChess are all good and have lots of features. ChessBase is a more advanced one to build libraries of games and a depth of analysis sure to challenge even the most anal of players, but can be pricey.
About sites, I had not been on a chess site in a long time, but that chess.com one has plenty of low-rated people too, games seem to be plentiful, and the site functionality/interface is better than I had originally feared.