I just went into Google Maps and asked for direction from San Diego to New York, avoiding highways. I'm 1400 miles into it right now, in the middle of Kansas and everything is okay except for an excess of flat tires, and a shortage of bicycle shops.
I've just been sleeping wherever. My best night was actually in a big culvert in Colorado. It was stand up height, and empty and dry inside. Good for a small fire that wouldn't attract attention I gambled a bit on it not flash flooding, but I had all my stuff packed up and ready to move out if it did.