I started haying just a few years ago. Previously I used other people to do the haying (cut, ted, rake, bale). The deal was a 50/50 split AND help me get mine stacked up in the hay mow (on site). That was for 16-17 acres of neglected grass and plenty of weeds. Well, that was the plan anyway. Even though the balers were getting much the same hay elsewhere, they probably had larger fields, their own fields, families' fields, free fields, and possibly paying ones to do first. I always seemed to be LAST. So, there was never more than one cutting and it usually wasn't until late August or September, if at all. Some years they never showed up. By then the hay was pretty much just indigestible fiber. And the weeds have consequently gone crazy. Now add to that a new highly invasive Pale Swallowwort that is taking over and crowding out everything else. So far it's control has been a losing battle. Cutting just once or twice a year makes it spread underground faster. It's slow to come up in the Spring so you can't get an early start on the field, or frost seed. And it can't absorb enough herbicides until it is about to flower (when the hay should be cut), and the "crop" is too thick for the spray to penetrate. And of course, there is now an unending supply of seeds waiting to come up. So I have had to acquire my own equipment, learn to run and fix it.
In NY it takes 3 nice days to make hay. It can get hot here but the humidity is the killer. Day 1-cut and ted, Day 2-ted again (and that's for thin grass/weeds), Day 3-rake and bale. I have tried raking into windrows the day before, but the dew won't dry and I just have to re-ted and wait.
Since I have been on the farm, the weather each year has been weirder than I ever remember. We get dumped on with 3 feet of snow in late March, so no frost seeding, can't get into the field. We've had summer droughts, so grazing after first cut was a bust. This year Spring rains finally ended just a week ago. We were so wet I didn't dare take any real equipment into the field. I barely got in and out with a 20hp with turf tires and was still leaving big ruts. My neighbors who tried to start haying lost the hay due to rain or spent the day trying to get the tractor back out.
And then you get to the equipment. My funds only allowed for auctioned used pieces. They are all there for a reason, it's up to you to figure out why.
I am using a NHTN75DA (boy do I love having a cab with heat/AC); Gehl 2170 sickle mower/conditioner (it works well but does have some joints that won't take grease), NH254 Rake/Tedder (jack of both trades, master of none, but good enough when the rake failed. Needs regular cam follower and occasional whole arm replacement--my field was not well prepared at last till, plus lots of rocks); side rake - unidentifiable make/model (works, needs regular tine replacement); JD348 wire baler (avoid this model, chronic problems); Hay/grain elevator (on my 2nd--chains are expensive, with 3rd motor); assorted landscape trailers instead of hay racks; I also use the JD4100 to pull the side rake. It has a hard time on the rolling hills, but is more nimble than a larger tractor. I could really use more tractors, it's a pain to stop, drop and change equipment. Plus, if I actually had some help it would be nice to be able to put them to work.
Most farmers in this area are going to round bales for themselves. It's hard to find anyone willing to help hay when it involves hand pick-up, unloading, and re-stacking. I could never use the kicker on my baler, it screws up too often. But my only storage is up in the mow, so it has to be small squares. I wish I had bought a string baler instead of wire.