Yeah, I've got a set of Hayes brakes I bled in 2001 or so that have't needed a bleeding at all. If you're bleeding them that often, 2-3 times a year, you might have a leak of some sort.

I too try and break in pads, which helps, but there's an issue if you only get 5-6 months, meaning 20-25 rides, and you're losing power. What brand are we talking?