I also agree with Vito. This first year with the wedding coming I would just have it done by someone. You have not said how much of your ground is in hay or pasture. For just three horses you should have plenty of hay. I would start at the local feed store, not the chain one the old time one. Ask them if they know anyone doing hay on the shares. If you can find someone to do it on the halves you not only get the hay put up but you get some experience on hay making. That knowledge will help you chose what equipment you need.
As far as tractors. I would hold off there too. A cheap old tractor can just be a money pit that someone else is dumping. A Ford 8n was a fine tractor in 1952 when they where last sold but newer better tractors can be had for not that much more money. I know that some 8N purest will trash me. Those 8Ns are not a good tractor for a novice to start out on. They don"t not have live PTO or lift. The brakes where not the best new let alone sixty years later. No power steering. Geared way too fast in reverse. Example: I would love to drive a Model T car in the July 4th parade but I would not do it in Jan. 20 below at six in the morning going to work. So for the collector hobby guys a 8N is fine but to use for real they are a pain. I know this how?? I had to use one early in my farming life. Owned several since then but not to use.
You can find a later Ford 661 or 861. A MF 135 also. All of these would be much better for you to use. They have live hydraulics and PTO. Much better gearing. You can find them for just a little more than that 8N.
Mowing modern thick hay with a horse drawn mower is tough to do. Clover can make you find/lose your religion. LOL Also it really helps to have it conditioned to dry faster.
A budget of $6250-8500 should get you a good line of used equipment. Here is a price range and some model listings. Tractor: $3500-4000 (Ford 661, 861 or MF 135) Sickle bar mower: (good one) $500-1000 ( NH 451, JD 350, IH 100) Side delivery rake: $750-1000 ( NH 56, 256, JD 894, IH 14) Square baler: $ 1500-2500 ( NH 67,267,273, JD 24T, IH 37,47, MF 12)
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