Biggest takeaway: the idea bordered between impractical and stupid. But I was 24 and I thought I knew better. Also, I was 24, I could tolerate being stupid.
Other takeaways:
1. Buy a Costco 24 Hour Fitness membership. You now have access to facilities around the country.
2. Make friends with 7/11 clerks, the nice ones got your back at night for a few days at a time.
3. Pack a baseball bat. Seriously.
4. Bring a tent and camping chairs.
5. Very few bums and vagrants have good stories but the ones that do are worth their weight in gold.
At the end of the day you're going to spend more time and effort figuring out how to survive than working. This becomes a huge drag after the magic fades the first week.
And, oh yeah, if you want to be full on relentless: make friends with big corp employees in Mtn View and Palo Alto to partake in their cafeterias. Or figure out how to do the tailgating dance.