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Water pooling, uneven surfaces, or basement leaks are indicators.

Yes, you can rent a rototiller for around $60 per day and do the work yourself, but it’s not recommended. Tilling is more of an art than a science, as tilling too deep can be detrimental to your soil structure and the organic matter that is beneficial to plants and shrubs, and tilling too shallow won’t properly introduce fertilizer or break up the soil for rooting plants. Additionally, tillers are powerful machines with sharp blades to cut through small roots and soil, so they are inherently dangerous to use. It’s usually worth it to hire a professional rototiller.

Many ways to landscape a steep slope on a budget exist. Avoiding expensive retaining wall construction is the first step. Consider creating a rocky slope with boulders or large stones, or think about planting perennials that return every year with a single investment. Transplanting small trees from elsewhere on your property is also possible and can help to stabilize steep slopes without purchasing new ones. 

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.