Yes, one must do such sessions to clean leaves from various places if you have a large open area. But this is good to stay fit. We have a vacuum leaves collector which does our job easier. We don't have a cart and no fire allowed (but only in BBQ outside of the home), we collect everything in green bins.

We haven't such a large area back in Canberra (850 meters open and 450 built-up) but due to very strong winds (up to 60-70 km/hr sometimes) and too many trees, we have to do it almost every fortnight. And the kind of standard tiled roofs which you know need more care due to leaves in chocked rainwater pipes. This is besides what the council's cleaners do every week.