I think the problem there is one of scale (same as here, actually). Hardly any small planes get built. Cirrus is the largest builder of small airplanes and they sold 276 new aircraft in 2013. These planes cost hundreds of thousands of dollars, but even if you slashed it so that new planes only cost $50k, you still have two huge hurdles:
1. There aren't very many certificated pilots in the US (600k?), and a small fraction who fly regularly enough for owning a plane to make sense. Not a huge market.
2. This does nothing for operating costs. Fuel, maintenance, insurance, storage all mean that even for a small airplane, you should expect to spend $100 - 300 / hr for operating costs, depending on details of the plane and how often you fly. This means that the market really can't expand that much.
The best hope for putting lots of new airplanes in the air every year is a viable self-piloting VTOL electric aircraft. I don't see anything else doing it, and energy density of batteries means that we're probably decades away from that.