I assume you're considering a concrete pool? You can't drain a fiberglass pool in flat ground, except in arid areas, and you can't drain a vinyl pool at all.
+ Pools can function with or without a main drain, but it's much harder to drain the pool without one. A MD also improves circulation; without one the deep end can be rather static. Do they help with cleaning? Not so much.
+ If you have leaf and seed debris, definitely get a pressure side cleaner with its own bag. Only those cleaners have the capacity do hold a fair quantity of leaves without stopping anything else up. A pressure side cleaner also improves circulation, so if you have one, a MD doesn't matter as much. (But you still can't drain the pool without one!)
+ All 3 majors have some good equipment and some junk, though I personal prefer Pentair & Hayward to Jandy.
+ The more skimmers, the better you'll collect leaves, etc.
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