re: Best way to start investing with $1000

The book selections are good. I would add that if you are just starting out it may not be a bad idea to set aside some small amount (a couple of thousand is fine) and actively trade it. Set aside a similar amount to invest in index funds.

Why? Because you'll eventually convince yourself that beating an index fund consistently isn't at all easy and exposes you to much more fluctuation. It's less expensive to learn this lesson now than when you're retired with a few hundred thousand and nothing better to do. I've seen guys in that position literally bet everything they have (leveraged even!) and have real roller-coaster rides with their life savings. Get this out of your system now while the tuition is cheap.