We’ve bought 3 homes with pools. I usually ask how old the pool and equipment are.
What size the pool is.
How old is the liner, does it have any patches?
Have they ever replaced any pool equipment?
Any issues with the pool coping or concrete/tile surrounding the pool?
Visually inspect the pool equipment- the multi valve port lever, the lid to the leaf collection pot, is it free of cracks?
Ask how old the sand is if it’s a sand filter.
Is it a chlorine pool or salt water.
Single speed, dual speed or variable speed pump.
How is the pool covered? Is the cover in good condition? Is there a pool heater? Does it work? Any drainage conditions in the yard that run towards the pool?