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How do you empty the water in the kettle without making a mess? What about cleaning the bottom perforated tray?

We use a soft brush every night on all parts including the perforated tray. You should clean the kettle with a brush or cloth while it is warm according to the instructions from the manual I have.

Does the kind of oil you use make it more or less difficult to clean the popper?

I've read discussions about different aspects of oil, like flavor, customer preference, cost, healthiness, etc, but I don't remember seeing anyone discuss cleanup of different types of oil.

In my home kitchen, it always seemed to me that cooking oil is bad about baking onto pans and becoming difficult to scrub off. Whereas shortening or butter seems to come off much easier. So which oil comes off the kettle the easiest? Any difference?

Pure coconut oil will leave the least blak residue(and also give you the best tasting corn imho). Canola oil or canola blends lead to more carbon deposits. Have no experience with peanut or other oils.

The best procedure is to be constantly(after popping and cool down) wiping the exterior and interior with a soft cloth. This keeps the oils from building up and blackening.

Aside from the daily once over, we "detail" clean our popper once a week on a slow night making sure to get all surfaces extra attention.