Don't be mislead by how difficult it is to physically lift the tail. It takes two hefty blokes to lift a Chipmunk's tail off the ground, and while it's one of the more tail-heavy taildraggers, I've thad the tail lift more than once in strong tailwinds (and got it down again!), once through that rudder thingy I mentioned in my earlier post. Try lifting your pride and joy off the ground when she's in the hangar - can't be done. But 40 or so knots under the wings and up she goes.
Always treat strong winds on the ground with great respect when taildragging, at all times that you are not facing directly into it.
SSD