Not every Oak Hill lot is flat, even close to the lake
Oak Hill's terrain rolls more than people expect from a neighborhood known mostly for its canopy - properties closer to the ridges bordering Forest Hills, or lots that drop toward a creek feeding the Radnor Lake watershed, can carry real grade rather than the gentle, even lawns pictured when someone imagines a wooded estate lot. A stump sitting on one of those slopes is a genuinely different job than the same stump on level ground, and treating it the same way is how equipment ends up sliding, chips end up scattered downhill onto a neighbor's property, or a lawn gets torn up trying to force a machine to sit level where the ground won't let it.
The first thing we do on a sloped job is walk the actual grade around the stump, not just glance at it from the driveway, since a slope that looks manageable from a distance sometimes turns out steeper right at the working area than anywhere else on the lot.
Footing comes before the stump does
A grinder wants to sit level and stable while it's cutting, and a hillside stump rarely offers that without some adjustment. We'll often approach from the uphill side first, working the stump in stages rather than trying to grind it evenly from one fixed position the way we would on flat ground, and we chock or reposition the machine more frequently than a flat-lawn job would ever require. That slower, more deliberate pace is the tradeoff for keeping the equipment - and whoever's operating it - stable on ground that doesn't want to stay still under a running machine.
Wet weather makes this considerably worse. A slope that's manageable when dry can become genuinely unsafe to work once rain has softened the surface, so we're more willing to push a sloped job back a day or two for weather than we would a comparable job on level lawn.
Chips travel differently downhill
Gravity does some of the spreading work for us on a downhill grind, which sounds convenient until the chips end up scattered further than intended, potentially into a neighbor's yard below or into a drainage path that carries them somewhere you didn't plan for. We contain the spread more deliberately on a slope than we would on flat ground - working in a direction that keeps material moving toward a controlled pile rather than letting it fan out downhill - and that containment step is part of why a sloped stump takes longer than its diameter alone would suggest.
We'll sometimes stage a tarp or a barrier on the downhill side before we start, specifically to catch material that would otherwise roll or blow past where we want it to land, rather than chasing loose chips down a hillside afterward.
Root systems on a slope don't grow evenly
Trees on a hillside often develop root systems that are asymmetric by necessity, with heavier growth on the downhill side for stability against gravity's constant pull. That means a stump on a slope can have a root flare that's noticeably bigger on one side than the other, which affects both how long the grind takes and how we plan the approach - starting on the side with the deeper root mass rather than assuming the flare is roughly even all the way around the way it might be on a stump grown on flat ground.
We've learned to expect this asymmetry on Oak Hill's sloped lots specifically, since even a modest grade change is enough over the years to push a tree's root development noticeably off-center, and quoting a hillside stump as if it were a flat-ground job of the same diameter tends to run short on both time and price. It's one more reason we'd rather see a sloped stump in person before committing to a firm number than guess purely from a photo taken looking down a hill.
The short version
A stump on a sloped Oak Hill lot needs slower, staged grinding, deliberate footing, and controlled chip containment rather than the same approach used on flat ground - and wet weather is reason enough to push the job back a day rather than force it on unstable footing.