Only after I identify software that fills my needs do I start to shop for licenses. I went through a phase, years ago, where I would only do things with my computer that I could do with free software. That meant, if all interesting videos were Flash, I couldn’t watch videos.
I also believe you have to choose the right software—even if it means using something proprietary. What’s the point of using a tool that doesn’t do what you need it to do?