If you really want lengthy rappels, get into caving.  A fair number of cave trips start off with lengthy rappels. The longest I have done was 503 feet, straight down.  There is a pit in Mexico, Sotano des Golandrinas (pit of the Swallows) which is 1000 feet to the bottom.

Of course, you have to climb back up.  Whenever you rap, carry and know how to use, ascent gear.

 

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