Sorry, totally missed this, although personally I have no experience in the States (just yet!) But I do think your ideas are pretty cool.
As for hostels paying, im not so sure. Ive only found hostels will give you a bed for free, and maybe a free t shirt, but not actually paying money.
Ive heard some great things about Coushsurfing, so thats a definite.
Im sure you will be able to find odd jobs/casual work wherever you go. Sorry that im not alot of help, im sure other tpunks will come along with some ideas.
p.s When are you starting this? I would love some info as you go along, as I will be in america for 2 months starting april.
Ive been to: England, France, Italy, Scotland, South Africa, UAE, USA - 14 states inc Hawaii, Vatican City
Currently Working in England
After:Jan 5 - South Africa. Sometime 2012 - Canada!