The John Deere website lists a new 2018 for $2,999. Figure a little wiggle room, and what would a new unit cost? As to the big box store offerings, most of them are pretty low grade models, plus the fact that you will have a hard time getting service work done. John Deere doesn't want to do warranty work on something you bought from Lowes, and the same goes for other brands.
The X330 has a Tuff Torq K46 transaxle in it. That unit has a poor reliability record. Google K46 problems or even search this site for discussions on it. They are non-serviceable and can do fairly well on flat land with no heavy cart towing, but you mentioned you have a slope to deal with. I know you would be exceeding your budget, but an x370 would be a better bet for you. You have power steering, hydraulic lift and a better K57 transaxle.
If you look at the used markets, you'll see tons for these big box tractors for sale. Why? Longevity? Certainly the used market will offer some heavier units at a decent price. I would do a little reading on the K46 before you make a final decision. Out of warranty parts for a K46 fix will cost you upwards of $400. A dealer installed replacement will run $600-700 or more. The K46 can become a pay me now or pay me later deal if you decide not to upgrade to a better model transaxle.