When I face the same PITA again and again, I ask how I can do it differently, or use to my advantage.
I had a Port Orford Cedar on the corner of a house, laying on the roof. Rather that clear the whole bottom at the beginning, I left the limbs over the roof, and cut a wedge around the tree. The rest of the limbs above rolled off the low limb to the grass without rigging or much handling.
Cutting top limbs to fall on the bottom limbs lets them come to rest. Sometimes you can cut a bunch of limbs, letting them fall onto lower limbs, prune the stubs, hang the saw, throw to the drop-zone, and onto the next set.
Always clearing out a path for stuff to fall is only helpful when you want stuff to free-fall. For that matter, a roped piece coming fully free Every time is not always ideal, especially is self-lowering.