Depending on where you live in upstate NY, I would be concerned. Here in the Catskills, the soil is amazingly fertile, especially when you consider the fact that there basically isn't any soil at all. It's amazing how well stuff grows here, especially cool weather crops like salad greens and cauliflower and such. Equally amazing is the number of critters that eat all the stuff you plant, from slugs and snails to mice and chucks, rabbits, turkeys (they like berries especially) and bears to name a few of the culprits. We've had good luck with the Troy Bilt walk behind that Mom bought in 1978, back when Troy Bilt was top line stuff, but tines wear out very, very fast and the porpoising of the machine, even in the garden that has been under till and cultivation since 1978 is amazing. I wouldn't use a tiller on my tractor around here, and I'm gradually switching to raised beds for most of the garden, so tilling will be minimal in the years to come. The 34 year old 7hp Kohler on that Troy Bilt is all original except for the electronic ignition module I put on it a few years ago and starts on the first pull every time.
On our land here, you could walk around all day trying to find one place you could stick a shovel in the ground and dig. Wouldn't want a tiller on my tractor here.