I've read most of the stuff on this case. I just thought I'd chime in on some personal experience from being on the road for a few weeks. Last summer, I drove from PA to Colorado. I spent 17 days on the road, driving all around the state and into Eastern Utah. Of the 17 days, I roughed it all but 3 nights, which I spent in a hotel. I either, car camped, slept in my car at a rest stop/Walmart or backpacked out into the wilderness. You can actually sleep in Walmart parking lots, so if he tends to frequent them, that could be a possibility too.
Anyway, I only spent about 1,000 bucks on that trip and actually about 300 or more was spent those three nights in hotels. I did go grocery shopping before the trip and actually took a ton of food out there. So, depending on how much he actually brought beforehand, would depend on how much he'd have to spend. Next to those two items, gas was my other high priced item. Obviously if they stay put somewhere, they won't be burning through any more money on that. I could've definitely done the trip spending far less than I did.
If you are willing to rough it, you definitely don't need to spend a lot of money. Granted, I can't see him and her doing that too well. I'm kind of used to it, as I probably spent 40 nights last year either camping or sleeping in my car. Also, he does have to feed two people, not one (if he's the only one with $).
If he is out west, there are lots of National Forest lands. They allow you to stay, even with a car at certain spots for up to 14 straight days for free. Some of that is hard for them to enforce, especially in the mountains just outside of populated areas like Denver. A lot of drifter types in those National Forests for LE to keep track of.
I definitely think they could last a bit longer with the $ they brought along, if they knew what they were doing and it wasn't something they were uncomfortable with. However, I don't really think that is the case for them, as I think this would be a big lifestyle change for them.
