What I picture in my head is bouncing around the US doing 3-6 month contract jobs after college.
Anyone else do this? Or has any advice on how to kick start this?
The concept is simple...
It's all the information I need to be able to work effectively from anywhere in the world. Internet or not. I plan on cleaning it up one of these days and posting it to Github or something but essentially it covers some of these topics...
Hardware : Best hardware for traveling. From most efficient machines, to best travel HDD for size/cost, backpacks, roll-up solar panels for emergency charging, etc...
Software : A massive offline collection of documentation. All searchable through an interface like Dash, (also with alot of Stack Overflow material), offline dev environments (like localstorage for assets), etc
Various Tips : Like how Starbucks doesnt turn their wifi off at night. So when I take fly fishing trips through the appalachian trail I can usually drive to the nearest town and find a Starbucks to push the code I wrote that day.
* You should figure out what you want to do, or what you want out of this experience, and then figure out how you'll do it. If I were you, I would pick my top 2 cities or startups and then do everything I could to find work there.
Web development is really friendly to the idea of remote work, but you have to be very good at what you do (otherwise most companies will hire someone of equal or higher skill, for a similar price, who will be willing to work on-site).
I'm not trying to stereotype you, but the majority of people that I talk to (and my own experience echoes this) have not typically seen the kind of output from recent college grads that would justify a company supporting the lifestyle you're envisioning. You should be really comfortable working on the web, and able implement fairly advanced techniques on your own, before you start backpacking around the country as a lone-gun coder. Know what part of the stack you're best at, and be really freaking good at it; then you can demand what you're asking from would-be employers.
I think the most important thing is to have a solid network of recruiters to ensure a steady stream of jobs. Over time you should be able to carve out a niche and get more work organically but at first you'll be relying on recruiters to keep your pipeline full.