I have the 2305 and can say it's overkill for the 2 acres I finished on my 5 acre lot. The loader is great for moving stuff around, but the same can be done with a tow-behind trailer. Maybe not as easily, but the smaller machine size on 1/3 acre will be much easier to deal with. 1/3 ac is tiny! I'd have gone nuts if I'd had the 2305 on my previous 1/2 ac lot. Get a heavier garden tractor (aka X300 series?) with a SB, chains, and a locking differential and I think you'll be fine on the hills. And far happier with the appropriate sized machine for your lot. You'll also have plenty left over for snacks to put on the new machine and landscape material...