Getting your foot in the door of web development is difficult but not impossible. In your situation, honestly I’d just move to a better city any way I could. If you have to leave all your stuff behind and go live with a friend and crash on his couch, I’d say that’s better than all your other alternatives.
If you could get a web dev job in your current location, that would be ideal. Next best option would be to get a job in another city and negotiate having relocation expenses be paid. But that would be a tough sell for a junior role.
If you want to try this, I’d start talking to recruiters. Put your resume and portfolio up on Monster and LinkedIn and take any phone calls you get. Don’t be picky, take the first job you get offered and move wherever they want you to move. If you don’t like the job, start talking to recruiters again the very second you start working there.
I went from working at Panasonic in the test department to my first Ruby-only job this way. I had to drive to another city on Monday, stay in a company-provided apartment for the week, then drive back on Friday so I could have a social life on weekends. It sucked. But it felt sooo good once I had a job at home, doing what I loved, and a short commute.