If you haven't already planned to, I would highly suggest a heater for the pool. We are in Ottawa and can swim from about early May to late October. The heater really helps extend the swimming season.Interesting you're covering your pool by mid to late October. I know your fall comes a little later than ours in VA, but I was thinking, in terms of temperature, to get my pool closed down by the start of October. Our peak week for color, in mountains nearby, is mid-October. Right here, it's about the same or a bit later. So I figured it would be best to get the cover on by the start of the month. By then, it's cool enough to not go swimming that often.
Most of the trees in that area are less than 30 years old, but they're tall, so that height will the the problem more than the span of the branches.
Out of curiosity, about how far away do trees need to be to reduce the leaf and debris issues? I don't know if I can trim or cut too far out from the pool, but I can see how it goes.