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Typically, the best type to trim bushes is when they’re dormant. Winter and late fall, potentially even early spring are the best times to trim your bushes. These seasons allow you better access to the branches, as all leaves are gone and the branches are more brittle, making the trimming process easier. 

The legality of blowing leaves into the street depends on your city or county laws. Many cities have codes that restrict blowing leaves into the street because it can obstruct the view of nearby drivers and make cars dirty, not to mention angering neighbors. Violations can result in a fine or other problems. You can check the codes on your municipal government website to learn more local guidelines, but avoid spraying leaves into streets for now.

Several tools exist that can help remove unwanted grass. The one you choose depends greatly on how much you need to remove and how hard you'd like to work. A sod or turf cutter is the fastest method while using a shovel is labor-intensive and much slower. You may also need a garden rake, tiller, and wheelbarrow. 

Debris removal is often included in the overall cost of having a tree removed from your property. However, tree maintenance service companies do not always include debris removal in their pricing, so ask any contractors offering tree trimming cost estimates whether or not removal is included. If you want to keep the wood mulch, ask if they charge extra for it as well.