RobA,
We go 50/50 around here. I would advise against buying the hay equipment not only because of the investment but also the maintenance is very high on hay equipment. I'm a DIY kind of guy but hay is one thing where I draw the line. You are fortunate to have Amish folks around, most fortunate.
One word of caution from a practicing rancher...if you don't fertilize or add nutrients back into the hay fields, you will soon deplete them. Your Amish friends know this full well and probably would be very agreeable to adding some natural fertilizers to your fields from time to time.