PICkit is probably the best for you to start with. Debugger is useful of course.
Dont forget MPLAB also comes with simulator where you can step through your code to make sure it is 100% working.
Books, I bought 2 a while ago and they ended up in the bin. I didnt find it very useful at all, the style just didnt fit me.
Theres plenty of example off the net. The kit you get from microchip should come with tutorials, usually flashing LEDs, reading analog/digital inputs, etc etc.
Once you got the hang of it, bet you wanna play with USB, cant do that with 555s