Buying everything all at once sounds pretty attractive, but the reality is, you will still do a lot of learning, tweaking, and buying. And yes, probably shivering.
I like to compare hammocking to shooting primitive firearms...you just cannot buy your way into proficiency, and in truth, that's one of the things that I like the most.
If you can, try to go to a group hang before you write that big check, and try out a variety of stuff...you'll be glad you did.
Liars figure, and figures lie, painting false pictures. ;)