On the contrary, winter is the best riding season here. Never been swarmed by black flies on the snowmobile trails.
Don't know enough about elsewhere to compare the riding (born, and continue to live in Springfield), but I do know lots of "flatlanders" come here for their cycling vacations.
As for staying: taxes are high, energy costs are high, wages are low. But I imagine most people think that is the case, where ever they live.