I wouldn't have thought you'd flip it. I harrow a fairly steep paddock with a narrow wheelbase tractor without trouble, so far! Did catch the harrow on my own back wheel due to turning too tightly, then mounted it behind a link box to keep the cables clear of the wheels.
Agree with previous poster, 10' is pretty big. Mine is 5', and it's not too good at corners. Chain harrows are definitely better than nothing, use it aggressive side (pronged side) down and it will pull out a fair bit of thatch if it's a hefty harrow. Or stick a couple of car wheels or similar on top to weight it down.