Ive managed to run a small farm for more than 30 years without once owning a 4WD tractor. They're nice to have around, but life goes on without. 4WD is very important if you're going to use a smaller tractor for a big tractors job.
Power steering is a must in my opinion. Loader or not.
Used tractors CAN be a money pit. They can also be a real big bargain. It's about he same game as buying a used car or truck. If you're looking at used, I'd stay with certain models that have a good reputation, PLUS ones that sold many copies when still in production. That helps ensure a steady parts supply. (You will need parts eventually, even with new)
Certain brands are known for being easier to work on, besides being good tractors. That's where Masseys and Fords shine. They were built simple, targeting the smaller farm market. Most small farmers in the day, had a tendency to do most of their own wrench turning to save money. They bought tractors that accomodated that. Simple relates to dependable for some reason.
I'm of the belief that the best tractors for the buck were built in the 1960's and 70's. After that time, the "make 'em fall apart so we can sell 'em ANOTHER tractor" mentality started to filter in from the auto manufacturers.
The TO-30 was a shining star back in its day. But it just isn't much of a horse by the standards of later years.
I'll pass on one bit of info on "test driving" a potential used tractor purchase. Hook a HEAVY implement on the 3-point hitch. (Preferrably a PTO driven implement so ypou can check it out too) Lifts tend to work even with some problems, when there's no load. If it'll raise a heavy load and hold it up, the hydraulic system SHOULD be in good working order. I went with my son yesterday to look at a couple tractors he's contemplating buying. One wouldn't lift a 300 lb rear blade, even though it appeared to be working fine WITHOUT anything attached. (The boy wants MY tractors!)
Another thing I always look for with used tractors is "Does it start and run OK"? Generally, diesels that start quick are in good shape. (Not ALWAYS, but most of the time) Ones that struggle to get going are generally in need of help.
Paint, tires, seats, and other "replacable items" are cheap compared to crankshafts, injector pumps, hydraulic pumps, and the like. Outward appearances aren't nearly as important as good mechanical shape. Make sure the big ticket items are intact. THEN look at the appearance.