Have you considered using a power rake (with flails for blades rather than tines) to knock down the high spots? I don't know how high or large your high spots are, I only mention this because I renovated a very bumpy lawn last year. I killed off the existing grass and rented the power rake (again, with flails, not tines) just to break up the dead stuff, and I planned to fix the bumpiness later. But it turned out that the power rake did an outrageously good job of breaking up those high spots and redistributing the soil. Kind of like a mini rototiller. And after raking up the debris I found I had just about the perfect soil for seeding, so I just spread the seed and rolled with an empty metal roller afterwards to increase soil to seed contact. I was hugely impressed by that machine, for a few reasons, but mostly because of the way it knocked down those high spots.

Just a thought,
Paul

It is very rocky soil. The problems I have aren't with the high spots but rather the low spots. The high spots are the majority of the yard and will remain around that height. It's the ankle breaking holes and pits that need fixing

Oh, I see. For leveling I think you'll get better results with #2. Do you want as much of your existing grass to survive as possible?

I actually don't care if the existing grass survives or not. It's OK grass but not as good as what I'll be putting down over it.

Option 1 would kill more of it of course, but if you don't care if it survives then option two will be fine, at least for the leveling (I don't know whether those seeds are right for your area, but am assuming you have that in hand).

Cheers,
Paul

If you don't care about the existing grass the cadillac approach would be to till it and hire someone with a box blade to level it for you. Then roll, seed and lightly roll in the seed.

Less effective but less costly would be to till and level as best you can, then roll. This should get rid of most of the sharp holes which seem to be your main complaint (understandably). Of course, then seed and roll.

If its too rocky to rototill, you probably need to add enough topfill to get to a level where you could rototill for best effect.

Probably the minimum you could do would be to add enough dirt to fill most of the depressions, then use a power rake to somewhat level it then roll and seed and roll in the seed.