Yeah I am not pooping on the pool ( ) idea, but just realistically presenting what’s it like. I honestly do not spend a lot of time on maintenance - the main thing I have to do is skim leaves and clean out the baskets. I am pleased to pay my pool guy to handle the chemicals and keeping the water in good shape. I do have to drain it manually after a storm, since the pool construction crew failed to connect the overflow to the storm drain, but that is very occasional.
We have a vacuum that runs whenever the filter is on, so it picks up most everything that ends up on the bottom, and is removable for when people are using the pool. All I have to do is monitor and empty the basket on the vacuum hose, the skimmer basket, and the filter basket itself. I regularly rinse the filter cartridges - that is probably the biggest chore I do (you have to drain and open the filter and then hose-off each cartridge). Otherwise, it is not really a big deal to maintain. Once or twice a winter I need to get out the manual vacuum to pick-up debris after a bad storm.
I mentioned a solar blanket earlier - that was a hassle because it took two people to remove, so whenever I wanted to dip in the pool, I had to get someone to help, and then again to put the blanket back on (not to mention disposal and custom fitting when replacing). A couple years ago we got some of these floating solar disks to help heat the pool and those are much more convenient, and do a pretty decent job of heating the water, and keeping it from cooling too much at night.
Depending on your comfort level managing the chemicals (clearly, some are better at it than others), you can probably handle that on your own if you want to.
As for purchases, other than the solar disks, if you have a lot of kids using the pool, stuff for them to dive for are great, and I would recommend either swim goggles or snorkeling goggles for them as well - we still have a bunch of goggles from those days laying around here. In fact, snorkeling gear is fun for them as well (flippers), and I think Costco sells a set during the season. We also still have a basketball hoop that sits on the edge of the pool that my son and his friends still use. We have several inflatable rings that the adults can use to just float. I also recommend these sun protection swim shirts for when you want to stay in the water but have had enough sun. Anyway, just some ideas for entertainment.
All that said, my next house after this one, if there is a next one, will not have a pool.