Bite the bullet and cultivate. It will cost dollars but the end result will be satisfaction and a smooth pasture you can bale hay on.
Everything that eats is now gone....this is the first year we are not going to bail everything....that is why I am out in this field on a mower and really learning just how bumpy it is.
The "back" area is a real mess...this is really the first time I walked back there after I had brushed hogged everything (we did not even bail back there before, the tractor would fall in the holes and then the ends of the mower would hit the ground = bucket of not good. So this area has really just been left for over 20 years. I kid you not, there are areas back there that look like the ground was pushed up to a little mountain then right next to it, a deep hole, then another high point....between you could put your foot and the bumps would be over your ankle....I am betting 6" deep at least. You can see the tops of some of these little "mountains" where the brush hog has hit and taken the top of it off....so it was higher.
This is pretty bad....I am really thinking that the box blade is going to be where to start back here....My new android OS just eats my phone battery or I would try some photos...but it was dead...perhaps later today.
The rest of the "yard" has been bailed for years. And on a tractor it was never that bad....on all my mowing machine (BX, JD650, 54" craftsman, 48" john deere) they are all pretty bad, but with the 650 being the best I think because of the wheel base. Someone suggested I run the air pressure down in the BX and try again...they have high pressure in them because of the loader loads.
There is always a finish mower option...I do have an 8N and a JD 70 , The JD 70 is not a mowing machine unless you own Standard Oil, so I could do the finish mower on the 8N and go that route....I can stand on the 8N and that takes a great deal of the shock out of things.
Then there are the regular mowers with a suspension....perhaps that is why those things exist...for like me......Mowers like the Ferris and the Simplicity have suspensions but I have no idea how they work....For the costs of some of those mowers....some of the Ferris are over $10k, I would want a demo on MY land then I would wright the check if I think it worked.