Pools affect resale, just keep that in mind for future reference. Some buyers are thrilled with the fact that there is a pool, others run as fast as they can.
It does NOT increase the value of your home.
Having a pool is a labor of love. If you love your pool, it's worth all the grief and aggravation of upkeep/expense. If you don't love your pool, it's a living nightmare for some. They are an added expense, electric-water-chemicals and, repairs when things break. And when things break, it could be from $20-1000's of dollars to repair.
Here on LI, if you have a heater(more $ to operate) your season can easily run from March through October. No heater would be May/June through late September.
BTW...I am in the pool business
I've had a few customers over the years that have actually kept their pool open all year with a heater.