I owned a couple different hay cutting machines over the years. If doing custom work in damp climates, like some of us do, speed is of the essence.
First I had a self propelled. Very cheap to buy because it’s yesterday’s technology. Worked okay with sharp super tiger shark blades, but a lot of maintenance. Couldn’t cut fast enough to make money
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Sold the SP and moved on to (2) different pull types. Both worked well. One was a larger center pivot and the second was a side pull. They were faster, but had drawbacks in tight fields.
Eventually I came to realize a front mower was still the best option for MY situation. I put it in front of a road speed tractor that wastes little time driving between fields. It was hard to find a rig with a front 3 point and PTO I could afford, but it’s long been paid off and overall a great tractor. I can remove the front mower and do other work with the tractor.
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Haying is a process of adaptation to your changing company model and size. Your idea of adapting is going to be what helps you succeed going into your haying business. Keep trying and keep gathering up more land. Anything I can do to help, just ask.