Al,
The new Toro "5xi" series, I believe, is pretty nice and durable. It would be a step up from the Wheel Horse and offers a 60" deck. John Deere makes an "x" series tractor in two and four wheel drive that mows great and would handle your work easily, and last forever. It comes with a 54" or 62" deck. They both mow fast (within minutes of one another) and would pick up the pace a lot from the Wheel Horse. They are the cream of the crop in lawn and garden tractors, but $$$$$$. Kubota makes several good machines in the size you are looking for. They are not quite to the level of the JD x series, but are great machines and mow fast and well. Worth a look. Several posters like the Cub Cadets, but my personal experience with them is that each model is different. Some are great, some ..... This inconsistency makes me leery of recommending that brand currently. I would not look too hard at the JD 300 series; they are good machines, but have a belt or two, which may increase potential maintenence issues. My dad has one, and it does fine, but the lowest "x" model is SIMILAR in price and much more machine. If you are looking used, the ultimate battle ax is the Gravely Pro "G". My dad also has one of these and after over 2000 abusive hours, it still runs strong and mows well. They are no longer made, and parts are becoming a little more scarce, but the NE has the highest concentration of used machines to consider. Each recommendation listed offers the option of a 60" deck, but keep in mind that a new machine may mow faster with a 54" deck than your old Wheel Horse would with a 60". This is because of things like hydro drive and increased blade speed, allowing for faster ground speeds. Also, know prices have changed, prepare to spend 6500+ on a top-end machine with the features you want and durability you need. Many folks with big needs mowing are buying the ZTR machines. My opinion is that they are fine, but on rough terrian would offer very little benefit over a conventional garden tractor regarding mowing speed. I had an x595 JD and a ZTR 60", and on rough terrain, the JD would mow within minutes as fast as the ZTR and I could till, plow snow, pull a box blade and use a small loader with it. THAT was an excellent machine, and after using nearly all of those I mentioned, was head and shoulders above the rest. It is also by far the most expensive. Used versions generally will not save you a lot of money, because they have such excellent resale.
John M