As far as I see it, I have this great opportunity to break out of the regular 9-5 job world, which I have always wanted to do. I have been working weekends on pearmarket.co, which is a website for small farmers to more easily promote their products online (I have recently open sourced the core of the project at https://github.com/thecolorblue/beetpress). Unfortunately, it is not currently in a place where I can dedicate all of my time to it and see any income. I would say I am 3 months of solid work away from having a good beta. I do not see this as an option as it would clear out most of my savings, and leave me in mostly the same position I am in now.

I have looked into doing freelance work, but as I am self taught my CS skills are not as solid as other developers, and my design skills are just about average. I am more product focused, I try to work as closely to the end user as possible and clearly define what they need. There does not seem to be a need for freelance product people (is this a good assumption?). It's also important to note that I am 28 and just got engaged. Moving is an option, but living on a spare couch for a couple months is not.

So I really have two questions. What would you do in my situation (would you stay in a smaller city?), and if you could start over in web development, what would you focus on?