If I am limited to 5 books, here is where I would start.
When to Buy, When to Sell, and The Nature of Risk by Justin Mamis.
Stock Market Technique 1 & 2 by Richard Wycoff
I am sure Daniel has another 5 in mind, so that should give you a good 10 to start with.
As for software, I like TC-2000, for end of day charting. It is good for general screening and chart watching. The software reviews may give you some other ideas.
Investors Business Daily and Thompson FN have some information on what funds are buying. Although if you follow the exchange traded funds
www.holders.com and
www.ishares.com you will get an idea where money is flowing/leaving from the charts.
Bloomberg.com, thestreet.com, have some good commentary.
I subscribe to both RealMoney.com and Morningstar.com, both are about $100 a year. RM is more applicable to trading.
Pristine.com has some trading tips/lessons, but I think their seminars are overpriced. Don Bright posts here, you may want to read some of his threads.
Overall though, investing/trading is like being a BlackSmith or Electrician or any other skilled profession. Experience, both yours and others will serve you the best in the long run.
Best of Luck