Sounds like my old dilemma exactly. Here they cut on half, or now even a third(they keep 2/3). My fields can be cut 4 times in most years. For many years I struggled to get guys to come cut it and before we moved here I was giving it all away just to keep it mowed and still had trouble. The problem is that most farmers are cutting for cows, not horses. Cows eat just about anything, so they don't care if it's weedy, stalky seeded out etc. So for them the longer they let it go, the less work for them.
Well two years ago I had enough of watching my pastures go to weed & seed, so my neighbor and I went in the "hay business". We did some things right and some things wrong and here are my observations.
Your ok buying a used tedder and rake(not much big that can go wrong with it/easy to fix if it does break). We bought a brand new drum cutter($3500) and it is a pure pleasure to use, 6 blades cost $1.75 ea, are reversible and take 10 min to change out....a fantastic piece of machinery. Then came the baler, bought a used(20 years new) Hesston 530 4x4 baler for $2500. First year the pick-up shaft failed...$600 and 3 weeks waiting for parts, then 3 days crawling around under the baler in July...NOT FUN. Then this year it was an ongoing problem of bales halfway rolled, stopping in process, then us having to dump unroll and try again. I spent a few weeks reading researching the possible problem, but never figured it out, then the drive chain broke and we parked the dang thing. So for the rest of this season I found a local farmer to cut our hay.
The moral of the story is that if you buy used worn out junk your going to have high blood pressure and a short Irish temper very soon. I like doing my own hay, and there is a market if and ony if you have a place to store it out of the weather...no one wants hay that has sat out in the rain a few times. Next year I am going to bite the bullet and buy a brand new baler. I know I will never get my money out of it, but it will work for me instead of me having to work on it.