Pool Water Line

Hello, I want to install a 3/4 or 1/2 PVC water pipe so I can add water to my pool without having to pull out the water hose and drag it to the pool. Does the location of where I install this water pipe matter? I plan on renting a core drill to drill a hole through the side of the pool above the desired water line level. I am also planning on using the core drill to drill a 1-1/2 in hole to add a suction line for an automatic pool cleaner. Any suggestions of directions to properly drill these holes would help.

Thank you.