As far as getting someone to hay it its possible but may be a function of how clean the fields are. If you have a lot of brush or rocks most will probably pass. That stuff is hard on equipment and most would not risk it for marginal hay on a small pasture.

If it was me I would rent a tractor from your local dealer for a weekend. Maybe a couple different ones just to get an idea of what you want and works well for you. A bush hog and a tractor for a weekend or two would clean it up nicely.

A good dealer should walk you through how to use it. Probably give you a demonstration of what to do and more importantly what not to do. They often have used ones on the lot that they are willing to let go for short periods of time. May requre a week at a time though.

This way you get it cleaned up and an opportunity to try tractors for next years purchase.

Also get a soil test. The test is free in Arknasas since its paid for by a fert tax. Maybe free or low cost for you as well.

Fred