Just from reading your post the thing that jumps out at me is marketing. I gave up on trying to be the cheap hay guy. It costs me 12.75 per 4x5 round plus fertilizer. Somebody is always willing to work for less. I went the other direction, best hay I could make, advertise widely, have the ability to deliver any size load for a price. Packaged into a 4x5 so it hauls well in the back of a pickup, or two wide on a semi. I grow very little of what I sell anymore. People are willing to pay and pay well for inside storage and just in time delivery. But, its that way with any crop.
I'd focus on taking the hay up a notch. Spend your money on a baler that makes a package you can transport, a spraying with Plateau every fall, see for good timothy and orchardgrass, and nitrogen fertilizer. There is no reason my trucks need to be going through east Tennessee to Florida and Georgia with hay at 55.00 for rounds and 6.00 grass squares plus freight at 3.00 a loaded mile and you selling rolls for 10 bucks.
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