Replying to Coming from UK to travel Route 66 - Advice/Tips wanted!

Hi
This summer (maybe August) me and 4 friends are traveling to LA with the intention of driving route 66 in the non-historic direction (W->E).

I have been doing bits of research but need some tips from people that actually live in the states.
We are looking at car hire but as we are 23 insurance is adding a fair bit onto the price.

I suggested buying a car at one end and selling/scrapping it at the other end.
So, we have about $1500 dollars to spend on transport (not including gas or insurance) as this is what it would cost to hire.
So I want to know if you can get a decent pick up truck for around 1000-1100 dollars (this leaves a few hundred for repairs etc?)

Also in general is there any places any of you recommend along the way. We're doing Vegas already.
We're into punk/rock and were hoping to get a concert or two in. What is Chicago like for live music?