When I was younger, we were pretty rigorous about raking leaves. I remember, at both my house as a kid, and my grandmother's, we'd rake them up, load them in the back of a small utility trailer that hooked to the back of the lawn tractor, and haul them back into the woods. Granddad had built some wooden sides that attached to the trailer, so it could hold more.
However, we haven't done any serious raking in years. My old house did have a small courtyard area, about 30x30, that was bordered by the house and a stockade fence. It would tend to accumulate leaves, so we'd rake that, at least. But the rest of them, would just blow away, rot down, etc. What little was left would pretty much disappear in the spring, after cutting the grass once or twice.
Now, I'm out in a fairly rural area, both now and then, so you can get away with that. In a more residential area with close-by neighbors, probably not so easy!
My current place has a magnolia tree near the house, and I've learned that thing is a pain! It drops leaves all year round, and they're hard to rake up. I've just been running through them with the tractor when I cut the grass, and then, if there's too much mess, rake that up.
The new place has a swimming pool. Last year, I delayed in getting it closed down and covered, and paid the toll with leaves. It's out in an open area, with no trees hanging directly over, but stuff still got in it. Once the trees started dropping leaves, I was usually out there every day getting them out of the pool. It was mid November by the time I finally got a cover over it. Even though most of the leaves had fallen by then, by the time spring came around and it was time to open the pool, there was a ton of them on the cover.
The weekend before the company came out to open the pool, the cover was completely dry. I should have taken it off right then, but waited a few days. Alas, we had a rain storm, and once those leaves got water-logged, they were a pain to remove.
I had the pool closed and covered this past Monday, so at least this time around, I won't have to deal with scooping leaves out of the pool. And I'm going to try and be more proactive in the spring, once it's time to take the cover off.