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I'm no longer based in Santa Cruz. When I got the job at Trulia my family and I moved to the Bay Area. I'm currently living in Castro Valley and taking BART in and out of the financial district each day.
The junior college I attended is Cabrillo College[1]. They have a really great Digital Media Department[2] with many passionate and knowledgable teachers and students.
In particular Cabrillo has an excellent web design teacher named John Govsky[3]. I can honestly say that John's passion for web development was genuine and contagious. He is the first person that I remember showing me that software development is fun, cool, and exciting as well as serious business. It was in his classes that my confidence began to grow as I realized that I really understood this stuff.
For networking in Santa Cruz I did 2 things. The first is that I started a meetup called 'Startup Santa Cruz' and had bi-monthly meetings at my house in my personal office and invited people from my web design classes. The meetings were never huge, perhaps 5 people at the most but I found my first job via a 'Startup Santa Cruz' event.
A fellow student named Brook attended one of the first meetings. It turned out that Brook is the owner of a local Santa Cruz Web Design firm called Brooktown Designs[4]. She was looking for a web developer and my obvious passion for HTML/CSS as well as my drive to organize the 'Startup Santa Cruz' meetup got me the position at Brooktown Designs. I was only there very briefly before I transitioned to the Android dev shop that I mentioned in my original comment.
The second thing that I did to network is that I started hanging out at NextSpace [5] which is a really cool co-working space located in downtown Santa Cruz. They have regular tech talks so I signed up to give a talk on (still new at the time) HTML5.
A couple of dozen people showed up to the talk and I ended up leaving with several job leads and connections with local web/app developers as well as a couple of designers.
Regarding Ruby, Python, or PHP I would just recommend going with whatever feels the most natural to you, which according to your comment seems to be Python (Flask). I prefer Ruby on Rails because I think it has the greatest abstractions but the main thing is to feel comfortable and confident with the tools that you choose.
My email is cgcardona [at] gmail. Feel free to drop me an email so that we can make the connect. I'll pass along any leads that I can think of.
Best of luck!
:-]
[1] http://www.cabrillo.edu/
[2] http://www.cabrillo.edu/academics/digitalmedia/index.shtml
[3] http://teacherjohn.com/
[4] http://brooktown.com/
[5] http://nextspace.us/nextspace-santa-cruz/