Hi!
I play chess too, FM 2308...interested if there is anyone else serious chess player here.
As for the programs I definetely recommend Fritz with Rybka engine. Chessmaster may be appealing for the begginers because it has a lot of cool features but program capabilities cannot be matched with Fritz/Rybka/Shreder...
For the learning material...what can I say...Chessbase...Mega database 2009 and study(at least that is the modern aproach to the game)
memorisation. Most of chess(as long as it is a hobby) is based on strategy/tactics that cannot be memorised but if you start playing seriously nowdays you have to know more and more opening theory to be able to compete with young players nowdays.
Luck...its a game of full information so I it should be 0:)