how do you properly maintain a water well system?

Answer 1

basically no maintainence. You should be aware of how long your pump runs between cycles and if the time becomes noticeably shorter you need service.

I do not recommend pouring bleach down a well as a regular practice. Very corrosive and not needed unless there is some problem of well is opened for major service.

Answer 2

Isn't really much to maintain. As long as your pump works and the tank bladder is good it should be fine. I have heard of people pouring bleach down into the well but have never done this myself. Keeping ants away from the contacts in the electrical box was my worst problem. They would get in-between the contacts and get fried and prevent the pump from kicking on.