'Shame about the Chipmunk, though I hardly think that it's being a taildragger was a factor in it's blowing over. Any aircraft which can generate a few thousand pounds of lift in a 40+ MPH wind, is going to get blown over it it's only held down by 150 pounds of stuff in pails! It sure is a shame that people who tie down planes don't learn this lesson much earlier, and save a lot of planes from being wrecked!
less common thus more expensive on maintenance)
I would not rush to judgement that maintaining a taildragger is more expensive. Oleos can cost a lot more to maintain than a tailwheel, and are much less tolerant of being "somewhat" airworthy. Nosewheels in general are also much more costly when you break one off!