Well here is my take. If you purchased a older tractor say 50- 80 horse, that tractor would do the bulk of the work and save your smaller tractor. You could use your smaller tractor for a back up, light task like raking and picking up bales. Some good older tractors for haying include John Deere 60, 720, 730, 3010, 3020, 4010 and the 4020. All the tractors were economical to operate, pretty rugged, and good for pulling a swathers and baler. The 60, 720 and 730 were great hauling tractors but really really light on the front end. In the hay field you would be fine, but say you tried to pull out the neighbor who got stuck in the mud, the you have to be careful because the front of the tractor tends rare up.
Not a John Deere fan. Ih made a 560 and a 656. Both are pretty food haying tractors.
Case made an 800, 730, 830, 930, 870 and 970. These would also be good haying tractors. I have an allis Chalmers 185 and it does a good job on a swather and baler.
These newer tractors based on experience are not near as rugged and tough they are sold as and true grit of yesterday's tractor.
As far a a cheap dependable and reliable swather, I kind of like the John Deere 1209. Keep your guards replaced and sickle sections sharp is the secret to cutting hay.
As far as balers go, both John and New Holland have made pretty good balers over the years. John Deere had the 14t, 24t I think a 224, 336 and 346. If I got my numbers right, all were good balers. New Holland made a 268 and a 273. They were good balers. Two thing or problems with balers. One you run too much hay in to fast choke the baler down and shear a pin. No harm done, just a pain in the rear unplugging the baler. Another issue, especially if the baler has had 1000 (s) of bales put through it is knotter trouble. The knotters can be really touch. If the baler is tying, it ain't broke don't try and fix it. If you start having knotter trouble, it can drive you crazy and generally takes someone who has been around a lot of balers to get it straightened out and tying again. When it comes to balers knotter issues can be a very common very frustrating problem. Ih and mf both made balers, but have limited experience with them. Case made a baler, and I'm not to proud of that one.
As for a rake, I would just pick up a little ground powered side delivery rake. John Deere, mf, i think new Holland all made them. New Idea made one and it is a dinosaur model. If you find one of those, it just maybe on steel wheels. Hope this info is helpful. I will try to answer any questions you may have.
