Slippy,
Do you need MFWD? If not, you can look at a 2WD JD6230, PowrQuad, cab, etc. for right around $43,000 (15% off MSRP). Adding a loader, second SVC, and other goodies will probably get you up back to $50,000. It all depends on how you option it out, what you're dealer will do for you, etc., etc.
The PowrQuad is a nice transmission. Of course, if you add MFWD, you're looking at closer to the $60,000 range.
If you're looking at 250 acres of hay, you really need to consider what equipment you'll be using and match your tractor to the implement's requirements. You also want really good dealer support (at minimum, good parts supply) for both your tractor and implements. When its time to cut, ted, and/or bale, you cannot afford to be waiting on parts.
I would consider one used 100+ hp ag tractor and then one or two used tractors in the 60 to 80 hp range. Use the big guy for occasional tilling needs, running a stack wagon, big haybine, conditioner/mower etc., the 80 hp guy for the baler & haybine, conditioner/mower, and the 60 hp guy for tedding etc.
If the terrain is flat enough, I would use 2WD for all the tractors. Possibly think of MFWD on one of them.
Just an idea....