I suspect it depends on your site specifically, but as someone with a lot of trees, a terrace, and windborn organics, I'd have loved a second skimmer in my pool
At the same time, I dramatically reduced the amount of debris by installing a cheap pool skim product on a return that creates a Venturi effect and collects debris on the south end, so even if you go with one now and later wish you had a "second collector" there are inexpensive options
Agree with SW. If you have lots of trees or the wind blows a lot from one direction and then switches to another direction then it is great to have two skimmers. For us we get a lot of wind from the southwest and a lot of wind from the northwest depending whether we are getting a warm front or cool front. It would be good to have a skimmer downwind for each direction.
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