I like #2. Infinite runway from freelancing gives you a lot of options. As someone leaning toward design rather than programming, you might consider plugging i

I like #2. Infinite runway from freelancing gives you a lot of options. As someone leaning toward design rather than programming, you might consider plugging into a platform ecosystem rather than building standalone. In particular I'm thinking Salesforce or 37signals, but I'm sure there are others. Both have big groups of happily paying customers doing real business, and a good framework for API or widget plugins. Reduces the marketing risk and lets you focus on improving usability instead of starting from scratch.