Not that doing hay isn't hard work, but it's not the do-all, end-all of labors either. Just because you have 250 acres of hay doesn't mean you have to do it all in squares or do it all at one time. Start out doing 20-40 acres and see how that goes.
It's good to get some first hand experience with it before jumping with with both feet, but I find doing hay to be fairly enjoyable and rewarding work. Let me clarify that I only do fescue/orchard grass/timothy hay and it is primarily fed to to cattle, so it is not on the same caliber as high quality clover or alfafa. You could do 250 acres of hay with an equipment investment of less than $10,000 - of course, I'm refering to a used mower, rake and baler. We figure it takes about 40 to 50 cents per bale to pick up and put in the barn, using locally available labor (I don't know if you have this available to you or not). If you are successful with selling that for $3-$5 per bale, you can afford to upgrade some or all of your equipment as you go.
Good luck and take care.
