I don't make a living, but I'd like to think I'm close (3-5x would get me there)
Anyhow, my strategy was to make both the web app and the desktop app.
The web app is free, which drives users to the site, a small percentage of which buy the desktop app. The strategy works well, in the sense that I can run everything on autopilot for a few months at a time if I need to.
On the other hand, I sometimes feel like the relative profits are kind of low for the number of users that I have.