We LOVE ours. We don't even bother to "winterize" since we typically only have a few nights that fall below freezing during the winter (January). We had it installed when we were building our home, and this will be our 7th summer in the house.
My husband and I were discussing this a few months ago and decided that it has long since paid for itself in terms of "was it worth it?". The pool itself wasn't outrageous (in the neighborhood of $12,000 for inground with vinyl liner) and we sprung for a screen enclosure as well. That almost double the cost.
The upkeep (due to the screen) isn't really that much. Either in time or dollars. And as for adding water... I RARELY have to do that. I did last year a bit, as we were in severe drought conditions. But usually, we get enough afternoon thunderstorms or rain from hurricane systems or whatever that I don't have to add much, if any. More like, I am back flushing it to dump the extra (like after Beryl that just went by us last week).
Our pool is smallish, but SO worth it not to have to lug pool toys in the car to a neighborhood pool, and not having to load up in the car in wet clothes/suits to come home. Not to mention, many community pools have restrictions on what you can have in the pool/pool area. Some even say no floats. Some say no food. Etc.
We have snacks, drinks and floats pretty much every time we are in the pool. Entertained by it every summer so far. Just pull the platter out of the fridge and carry it out onto the patio while the kiddos dig in. Or take all the kids a popsicle directly from the freezer--no worries about transporting anything.
We had a "community" pool in our last neighborhood (they FINALLY built it about 2 years before we sold our house there after years of promising...) and we used it a total of 3 times. It was such a hassle to load up the kids. It was too far at the other side of the neighborhood to walk. (It literally was over a mile one way, and in the heat of summer, dragging worn out kids down the asphalt roads isn't worth it, plus you have to carry everything else, too).
You don't even feel "refreshed" after you get home.
Now, my husband jumps in after he does a 5 mile run. Or after he mows the grass. Or after a workout in the garage with his dumbbells. And I can let the kids hop in for 20 minutes to burn off energy and then be done. It isn't any "work" to do so. Just tell them, "Ok, you can get it for a few minutes before we ____."
As far as I am concerned, there is no benefit to a "community pool" vs a rec center or club membership pool somewhere else that you have to drive to go swim.