Is corn silage an option for your location and land?     "Here" it would be much easier to get a custom chopper to come chop 20-30 acres of corn silage once a year than it would be to get one to come chop 20-30 acres of hay 4 times/year.

Not to mention storing it properly would be much easier dealing with more tons at once vs having a small amount to deal with 4 times/year.