I see you have a dream of moving back to CA, and you've stated that you don't like DC, but have you given any thought to other destinations with a good tech job market? I've heard that Austin, Denver, Salt Lake City and some other places in the heartland have good jobs and good quality of life, with reasonable cost of living. Once you've paid off the hair-on-fire portion of your debts (everything beyond the student loan), it might pay to take a week or two off and travel those areas to get a sense of the possibilities.
I'd also suggest splitting the difference on the loan repayments: Pay off the overdue bills, medical debt and credit cards bills as a first priority, foregoing even your 401k contributions. But once you are left with just a student loan, back off a bit to start funding your 401k to the match limit, and divert a tiny stream of cash into an emergency savings account. For most people, having a single debt that is reasonable size and interest rate, with long payment terms and is for a respectable purpose, is not too uncomfortable. At least, attack all the other debts first and then come up for air when you just have the student loan left and see how you feel at the time. I think you should have a plan to eliminate the student loan within 2 years or so, but once you're just down a student loan you don't need to give up free money for the sake of retiring it in 1 year instead of 2.
You acknowledge being shy, and you should think long and hard about how you can push yourself in that department. Join a public speaking class in the evenings at a local community college? Join a club devoted to a hobby or interest you might have? Having self-confidence and good communication skills will help with negotiating salaries and business deals, which will have great long-term effects on your financial position. It will also help with attracting girls, which implicitly seems to be another thing on your mind (based on some of the points made in your original post).
I get the sense that you are trying too quickly to go from zero to hero, having recently got on the frugality bandwagon: Plans to pay off all your debts, move across the country, buy a house in one of the most expensive housing areas in the country, etc., etc. There are lots of garages to tinker in between DC and California, and a lot of steps for you to consider in between. Pay off your debts, work on your confidence and public speaking comfort, and see how things go from there.