Tales and tips for Roaders.

My mate Rocket's recommendation for accommodation search and booking: http://www.wotif.com/

For comms on the road I use an Asus EeePC, with an 8gb flash HD, so there's no worry about travel trauma. Throughout America, most hotels have free wifi, but not so here in NZ where hotels charge between $12 and $30 per day for in-room connection. Your own email service works fine.
One alternative I use locally is a USB T-stick available from both Telecom and Vodafone, which uses a SIMM card you can run on pre-pay, between $50 and $150 for the stick depending if its on special, and running cost about $1/day with a 10mb daily cap.
The notebook also serves as a daily download dock for pics taken with my cellphone, easily done with XP. 3.2 mega-pixel is the minimum for taking good pics, more if you're into a lot of zooming, but your picture size will get a bit demanding for email.

The cellphone service across USA is pretty disjointed given each state's autonomy, and coverage is worse than you'd imagine out in the sticks. Global roaming is expensive, coverage incomplete, but Vodafone's partner in US, AT&T, is getting better.
Texting back home works fine where coverage is available, pics too, and is a great way for keeping in touch.