Landscaping in Illinois is wind, clay, and water that has to leave the foundation before it leaves the yard. A windbreak should not dump snow on the walk you use. Town yards are smaller, shadier, and full of tree roots that heave a path. Freeze and thaw open cracks in a walk by spring. The call is about grading, plants, and hard surfaces that stopped doing their job, not about a magazine bed.
Downspouts that end at the footing will fill a basement no matter how green the lawn looks. Keep the soil sloping away from the house, even where the lot looks flat. Clay holds a puddle. A dry well or a shallow swale may be the honest fix where a pipe would just move the puddle to the neighbor. Say if the neighbor's grade already sends water onto you.
Salt and plow piles kill the same strip of parkway grass every spring. Say so if that is the complaint, because a new lawn will die there again without a soil change or a different edge. Shrubs planted in the gutter splash zone rot at the crown. A tree rubbing the roof is a roof problem and a tree problem at once. Storm-broken limbs over a bedroom come first; a bed redesign can wait.
Illinois summers are humid enough for fungus on a crowded lawn and hot enough to scorch a new planting that has no water plan. Ask what survives the wind, not what looked fine in a week of soft weather. Edging and mulch decide whether the yard stays keepable after the first season. If the work has to wait until the ground thaws, say whether you are planning or whether water is at the foundation now.
Lead with drainage, a dead hedge, a heaved walk, or limbs you cannot leave overhead. Give the town and whether clay is the soil you fight. Water at the wall is the call that should not wait. Call the number on this page.