Consider negotiating a better deal for you with someone who wants to use your fields. For example, a penalty if they do not take a third cut by Oct off.
Buying a large tractor and equipment to cut grass seems like a poor option to me. Is there another crop that your land will support? Incorporating some of the suggestions offered by Dusty3030 are worth looking at as well. Maybe a mix of less cutting and better use of fields that are left.
Yes, bad option just to cut grass. We're city folks and just moved out to the country 5 months ago, so this is all new to us. I am sure whatever next tractor I decide on will do more than just cut grass. We plan on having a vegetable garden and there are a couple of downed trees that I'm sure the tractor could help with.
No penalty on the hay with current person. My agreement with him was simply to cut it and move it for FREE. Well, it hasn't worked in my best interests currently. Most likely I will terminate the relationship and find someone else. Wife wants a butterfly field and a wildflower field, so we will be looking into all that as well. Right now its just been all I can do to just deal with trying to get a handle on how to maintain the property. We came from a .25 acre residential lot to a 90 acre farm. Never thought in a million years I would be on a tractor and doing farm types of work...