Here is an easy way to cut many (wooden) tail wheels (bare with me as i have no pics[])

Get a piece of dowel or whatever you wish to make your wheels out of.

Mark the thickness of the wheel onto the dowel and keep marking it untill you reach the end.

Cut the dowel into halfs (maybe even quarters).

Drill a hole a fraction smaller then your axle.

Shove the axle through that hole (force it if you have to also making sure there is about 1-3cm of excess axle hanging out of the dowel)

Put the excess axle into a drill

Get a Band saw (or similar) and the drill (with the dowel in it) and make the dowel just touch the saw, then press the drill button and away it goes!! It cuts through the dowel evenly and quickly, BUT make sure you dont cut through the axle!!! Once you have done 1 wheel you can move to the next and so on and so forth