Not every stump is reachable from the driveway
A fair number of Forest Hills properties drop off sharply behind the house, toward a lower yard or a creek line well below the level the driveway sits at, and a stump down there can't just be reached by driving a machine across the lawn from wherever the trailer parked out front. Before quoting a job like that, we walk the actual path the equipment would take - not the shortest line on a map, but the route with a grade the machine can hold without sliding or tipping along the way.
That walk-through sometimes reveals that the obvious path, a straight line down from the back porch, is actually the worst option, while a longer route along a shallower contour further to the side is the one that actually works. We'd rather spend ten minutes figuring that out on foot before committing than find out halfway down with a machine already in motion.
When a compact machine walks itself down instead of being carried
Most of the time, a compact walk-behind grinder can descend a moderate bank under its own power, guided carefully rather than driven at normal speed, with the operator staying on the uphill side of the machine the whole way down so a slip doesn't put them in its path. This works for grades that are steep but not severe - the kind of drop common behind a lot of Hidden Valley and Tyne Valley Estates lots where the house sits on the upper pad and the yard steps down from there toward a lower tree line or a creek.
Even on a bank the machine can handle, the descent itself takes real time and full attention, more like guiding a loaded hand truck down stairs than simply walking a machine across level ground. We don't rush that part regardless of how routine the stump waiting at the bottom turns out to be.
When the bank is too steep for that and a winch comes into play
On a genuinely steep bank - closer to a bluff drop than a sloped yard - walking the machine down under its own power isn't a safe option, and that's when a winch anchored to a fixed point at the top gets used to lower the grinder in a controlled, deliberate descent instead. Finding that anchor point matters as much as the winch itself; a healthy tree trunk or a solid structural post can usually take the load, but not every yard has one conveniently placed near the top of the bank.
This approach takes considerably longer than either a flat-lot job or a moderate-bank walk-down, and it's not something we improvise on site. If a bank looks like it needs this treatment, we plan for it before the day of the job, confirming the anchor point and the equipment we'll bring, rather than discovering the need for a winch with the machine already halfway down an unplanned descent.
Sometimes the honest answer is a different tool entirely
A handful of lower-yard stumps sit in spots no reasonably sized grinder can safely reach at all, particularly where the drop is severe and there's no anchor point solid enough to trust a winch to hold. In those cases we'll say so rather than force an unsafe descent just to avoid telling a homeowner no, and we'll talk through the alternatives that actually exist for that specific site.
Sometimes that means a smaller hand-operated grinding attachment that can be carried down rather than rolled, sometimes it means a different access route entirely - occasionally through a neighboring property with permission, occasionally not possible at all until other work on the site changes what's reachable. An honest 'not like this, but here's what would work' beats a plan that risks the equipment, the operator, or the bank itself. We'd rather turn down a job that isn't safe to reach than force a plan that puts the equipment, the crew, or the bank itself at risk just to say yes on the phone.
The short version
A stump below a steep bank needs its access route planned before the job, not improvised on site. A compact grinder can often walk itself down a moderate slope; a genuinely steep bank calls for a winch-controlled descent, and the rare lot needs an honest conversation about whether the equipment can safely reach it at all.