I like this last post. Sums me up too. Of course I upgraded to some serious power over the years but I upgraded to some serious hay implements too.
Tha little tractor will run an older NH 66, a 335 JD or a 14T just fine. Don't plan on pulling a wagon, just bale on the ground and pick 'em up later.
The older small bailers are just fine for a small holding. I just sold a 66 that bailed like a top that would probably run with a Vee belt and a briggs and stratton. I sold it to an older couple with 5 acres and a horse that were tired of getting gouged by greedy hay brokers. They paid 500 for it. I felt good about them buying it. It filled a need for them and I knew it was going to a good home.
The older bailers are set for sisal and have double twine discs. They will run 170 poly all day. Use poly, Forget sisal. I've posted on many threads (on here) concerning older bailers and new ones. I count ties instead of sheep and I know knotters inside and out.
You want a sickle mower, not a disc. You don't have the power for a disc, especially a discbine. A sidemount sickle mower takes very little power. It also takes some skill to run effectively but it's a mastered skill. Once you master the technique, you'll be mowing as fast as a disc mower can. The Amish only run sickle bar mowers, pulled by horses with a forecart. It takes literally a few 'horsepower' to run one.
You don't have the tractor weight for any mower conditioner. They are heavy, you aren't. A plain jane sickle is what you want. Ken Sweet has plenty.
Forget any round bailer. One, they need some power and 2, what are you going to do with rounds anyway. You don't have any way to move or store them.
you want small squares, no bale wagon and some help to pick them up. A pickup is a nice haywagon. You'll need a rake. For a small holding, a side delivery NH or JD is just fine. They are ground drive and pull with a quad or your lawn tractor or your little tractor. You don't need a tedder or a merger or any of that crap, You want simple and reliable. Just keep the implements greased and in the barn when not in use. I keep my implements outside in the summer, but they are all tarped. In the winter they come into the shop where it's heated and get a complete service, all fluids changed, washed and greased (always after washing) and I never wash them during hay time, only when I put them up. The it's off to the barn to sit until the next summer.
I run big stuff with big tractors but I do it professionally. I started like you and grew.
Make it fun, don't make it tedious. I have fun doing what I do. It's always been enjoyable for me and I make good money doing it. I look forward with pride to bringing in a field of excellent forage. It makes my customers happy and me as well.
This probably sounds stupid but I feel closer to God out there in the field, all alone and if I make a mistake or I have a breakdown, I'm responsible, me alone. No one to blame, no one to pass the buck on. You take care of it and go on. That's what life is all about.
You'll have issues, we all do. Machines break. Far as bailers are concerned, I'm always around to offer advice.