A few thoughts:
1. Making hay, especially square bales, is hard work. If you don't enjoy the physical labor of it, you will grow to hate doing it. On the other hand, there is no more satisfying feeling than a barn full of square bales of high quality hay as the sun is setting.
2. Your Kubota BX tractor is a bit small for that much acreage, but you do not have to have 40+ horsepower as stated by others in this thread. There is high quality compact hay equipment out there that can be run efficiently with a 25-30hp tractor of 2000+ pounds. In fact, your Kubota BX can make hay, but the production rate would be too slow for 30 acres.
3. Every time someone takes hay tonnage off your fields, it is costing you, one way or the other. The nutrients either have to be replaced (some kind of fertilizer), which is expensive, or you are going to end up with a field that won't grow anything but weeds. If your field is hilly, you are asking for erosion problems in the long term.
4. With some time and studying, you can make better hay than you will ever get having the farmer down the road do it. Why? Because he/she will not have the same motivations as you will. If you are feeding your own animals, you have a big incentive to make sure you have quality hay. That means you will make hay when the timing is right for the hay, not when it is convenient. Most contract hayers bale for quantity per cutting, which means they will generally cut too late. It is more work to cut earlier and more often, but it will greatly improve your hay quality.
5. There is always a market for quality hay. If you want to sell your extra hay, you can quickly build a reputation if it is good quality. You will have repeat customers and they will tell their friends.
6. Old equipment is cheap (relatively) but is generally not dependable. And repairs may be difficult, costly, or maybe impossible. And remember, equipment only breaks when it is being used, which means you are in the middle of the job, that now urgently needs to be finished. New equipment, on the other hand, is expensive, but will be ready to work when you are and will still be operational at the end of the day.