Im assuming your climate must be considerably more mild than Michigan. Here we only get 2 cuttings and the second is much poorer than the first. I spent most of last summer assisting in a haying operation (after work of course) and that was on a 120 acre farm. There is 1 quite level 10 acre field that is used exclusively for hay and then another additional 50 less level acres on which sheep graze which is also cut for hay. In addition there are 70 additional hilly acres less suitable for cutting which is accessible to the sheep for browse.
For haying, the owner has a case 700 which is the main workhorse, in addition a case 800 and a case 400. Typically, horses are used for the first cutting with a sickle bar mower. The horses knock down less of the new growth than a wheeled vehicle. Horses are also used for raking, although a Kubota RTV 500 is sometimes pressed into service when time is really tight. The 700 is used for dragging the baler and hay wagon. Typically there would be about 100-120 hay bales in the hay wagon, where they are flung by the "kicker" on the back of the baler. Last years total harvest for the property was probably about 15 wagons worth so between 1500 and 1950 bales. Now I do think that the baler was not correctly adjusted and the bales are longer than they should be and really heavy to lift. Likely 70-80lb each.
All of the equipment is from the 50's and 60's and quite maintenance intensive. We had 1 quite spectacular incident when the baler picked up a hefty piece of hardwood and sheared several shear pins and got out of synch and bent a needle. The bent needle in turn smashed the string knotting tooling on 1 side. Getting spares for this equipment is quite the pain in the rear...
This last season, rain on a nearly daily basis caused a lot of issues with hay quality. Its hard to believe how much the drying hay is affected by being rained on, but I saw it with my own eyes. First cutting is late May/June and last cutting might be late September into October. By August if the summer is dry the hay will simply stop growing and dry out.
I think that with a change to a round baler (to reduce bale handling since there is basically no labor available) and the addition of a larger tractor with a good loader, the hay operation might actually be a viable cash crop. It would eliminate all of the current hay wagons and the back breaking work to unload the hay wagons and stack the bales in the barn. It would also eliminate the square baler and its kicker, certainly one of the most dangerous pieces of equipment to run on the farm. Everyone's time is worth something, and a LOT of time went into baling, unloading and stacking, often in a big rush with a thunderstorm approaching to rain on your bailed hay. Of course it has to be about 95F and 95% humidity at the same time...
I hope you are young or have a lot of willing nieces and nephews.. If not, mechanise and go with round bales.