Following this with interest as I'm in a similar position.
So far, I've just mowed parts of my paddock with a topper behind a little tractor. I can't have animals in it as I've got fruit trees, a wildflower meadow etc, so all I've done over the past 3 years or so is mow most of it on a sporadic basis, generally from April to September ish.
Where I mow, the grass is quite green and lush, but where I don't it's getting a bit tussocky, mole hilly etc. I think I will harrow this year, to remove old thatch, flatten the mole hills and tussocks, break up the rougher grass a bit. Hopefully that will be all I need to do...
I may also move the cutters lower in my topper as the grass is always quite long - though this risks catching the blades on something as my paddock isn't too flat. Maybe better to leave them as they are until after harrowing, if I can get hold of a decent harrow!