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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. 

You can leave grass clippings on the lawn, depending on their length. You don’t want to completely cover new grass and block it from sunlight, or encourage moss crowd out the more delicate grass. However, short clippings are usually fine to leave on the lawn. In some cases, they can be beneficial: Clippings can be a source of fertilizer and help protect the ground as young grass blades develop.

Mature lilac bushes that are large and overgrown are more challenging to remove than small lilac bushes. Large lilac bushes have deeper roots that are more widespread, making it harder to dig them up and remove them. If you don’t dig under and around the primary roots, then you run the risk of the lilac bush growing back. So, it is a time-consuming process if done correctly. 

For minor unevenness, you don't necessarily need to remove grass before leveling. You can apply a topdressing mixture to fill in low areas and even out the surface. However, for more significant unevenness or deep depressions, it might be necessary to temporarily remove the grass to ensure proper leveling and soil compaction. After filling and leveling, you can replace the grass or consider reseeding the area.