So, here's an alternative thought......

do you have another farmer in the area whom you would be willing to sublease this ground to for 1 year, maybe 250 acres each year, and rotate those acres?  Can you make out?  Maybe even if you break even on the rent, you might be just as far ahead if you don't have to spend a whole bunch of dollars on equipment.  Seeing as how you are organic, that might be a challenge. 

1) When you say you grow "hay", are you talking legume hay, or grass hay?  If grass hay, is there value in including a legume rotational crop in that mix?

2) If you are organic, how do you apply Roundup + 2,4-D ?

3) If you are going to pull the plow and disk out of the bushes, why would you need a no-till drill?

4) I would expect that applying the organic fertilizer might be your biggest challenge.  Maybe that is where you need to start with equipment needs?   I would expect that finding combines to hire would be easy enough - but maybe you need to spend time cleaning it first to pass organic certification requirements ????  

5) or maybe you don't plan to stay organic??