Thanks for the input everyone. It sounds like the consensus is that something around 75hp will be enough for my needs. Any more thoughts on brand? I stopped by the Case dealership yesterday (nothings open, but they are closest and I figured I could look at what was on the lot.) They have a 75C with loader for about $47k. Good grief these things are beasts compaired to my little MF245.
So far JD and Kubota have been recommended. Can you tell me why? I have a friend who started with Kubota, loved it at first but recently switched to JD. He says it's better, but I remember how he raved about the Kubota when he first got it, and I can't help but thing recent purchases are always the best thing out there.
Kubota has by far the largest share of market for tractors under 75hp in the US (evidently something around 50%), Deere is probably next, and the other make up the remainder. Over 75 hp, Deere sells the most. Deere and Kubota have the advantages of extensive dealer networks and well-developed parts distribution.
While everyone develops a preference for brands, the fact is that there are few, if any, "poor quality" brands since the tractor business is so competitive. I first chose Kubota years ago because it meant something to me that the company engineers and builds all its own products from the ground up. There are some others that do likewise, while other makes assemble tractors with components sourced from other manufacturers... and end up with decent equipment, at least most of the time.
With your comments about being a reluctant do-it-yourself mechanic, it should be obvious that having a good, full-fledged dealership standing behind your tractor purchase should be a priority, probably more important than which particular color of paint you fancy.