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Depending on the method you choose to remove grass, it may or may not matter whether the grass is wet or dry when you perform the task. A dryer lawn will be easier to negotiate with a sod cutter, especially if you're not planning to reuse the turf. However, using a shovel by hand might be a little easier if the ground is slightly damp but not so much that it sticks to the tool.  

Dormant seasons like fall and winter are the best times to dig up plants, including holly bushes. Plants aren’t growing during these seasons, so the removal process goes a lot quicker. Consider hiring a landscaping team to handle holly bush removal during the cold-weather months for off-season pricing deals, too.

This depends on how many leaves there are. Mowing over dry and crisp leaves with a bagging attachment saves most homeowners a lot of time. If you have a smaller lawn and few leaves to mulch, you can put the leaves into a stand-alone mulcher resembling a wood chipper and collect the mulch from a hopper. This prevents having to do multiple passes with a mower.

No, you cannot throw branches from your neighbor’s tree back into their yard, nor can you discard leaves or other plant matter that originated from their yard back over there if it happens to land in your yard. You are responsible for cleaning up plant matter that made its way into your yard.