Joan,
From your profile and your description of the land, I'm assuming that you are dealing with the Massey shop in Marshall. If you've been going past there, have you noticed that there is a New Holland, with a cab, at the gas station 2 blocks west of Smith's? I don't know anything about it, but it looks like it is pretty close to new, and it has been sitting in the parking lot with a for sale sign for about a month.
I lived in your area for over 30 years, and still work there. If I were looking for a new tractor, I'd head out of the county to do serious shopping, except maybe for a New Holland.
My dealings with the local Massey shops (same owner for both) have always made me feel like I'd been robbed ($18 for an ignition key, $22 for an O-ring, $38 for an air filter, and the list goes on.) They are nice people, but they sure get a premium price for everything -- however, I've got to say, they always had what I needed. The local Deere and Kubota, well . . . I'd look outside the county.
If you are partial to the red and silver colors, I can highly recommend D&G Equipment in Augusta, WV (
http://dandgequipment.com and about 25 miles west of Winchester). They sell the smaller to medium sized Mahindras and the medium to large size McCormicks. Lots of new, and lots of good used implements. Excellent service, and they pickup and deliver.
There are a lot of good dealers up and down the I-81 corridor from Southern PA down to Southwestern, VA. Just about every tractor brand is represented more than once in that stretch.
You shouldn't have any problem selling your present tractor. A free listing in the Valley Trader is generally all you need. Used tractors, even if they need some work, seem to sell real well in this area.
Unless you are real particular about a specific dealer, or brand, most all major tractor brands that have forums on this website are going to be good reliable tractors when purchased new. Just make sure there are a couple of dealers within 75 to 100 miles in case you need major warranty service.
If you can't do most of your own routine maintenance, ask around, and you should be able to find several good free-lance tractor mechanics in the area.
Good luck,
Knute