Sounds good on paper but....we all know how that goes
Anyone have any advice?

Here is the info from the "checklist" that i felt may be relevent:

1. Where you live? Long Island, NY

2. What type of grass you have? the green stuff (sometimes anyway)

3. What products you have applied to your lawn, and how much? These include fertilizer, herbicide, fungicide, insecticide, etc.
Nothing thus far

10. If your problem is with weeds, what type of weeds?
not when I take care of it

Solution:

12. Do you have a preference towards a synthetic or organic solution? no

13. Past efforts to remedy the problem. fill some lows

14. Are any solutions not feasible? (hand pulling weeds for 2+ acres, daily watering, etc.)
As always cost is a factor.

Thanks in advance for your advice.

Had you read just a little more you would have read that tilling is not recommended for turf. The end result of tilling is the surface you have now - bumpy with bumps on the bumps. The reason is that a mere human cannot control a rototiller perfectly. It will buck, jump, and leap around as it hits rocks, roots, clods, and soft spots in the soil. You will tend to stop and let it chew and chew to pulverize the soil into a fine fluff. As it chews the weight of the machine will push the blades deeper into the soil leaving a pit. Then you'll push on and it will buck up over a root leaving an underground peak. Finally when you are finished, you will level the surface perfectly for planting. The problem comes when the fluffy soil settles. It will settle into the pits and away from the peaks leaving a bumpy surface once again. This settling process can take 3 years to finish. Thus the best approach for a flat lawn is to work completely at the surface.

The best solution is to bring in a landscaper with a tractor and back blade. They will scrape the surface off leaving you with a perfect surface for planting either seed or sod. It takes much less than a morning to do that.

Your area is only 1,800 square feet, so it might seem like you could level it yourself. I suppose it could be done like this. Rent a tool called a sod cutter. A sod cutter takes the surface layer of sod off the ground and leaves flat soil underneath. If you are really patient you might be able to do a really nice job with that. In the end what you want it bare soil but not tilled. Start at the highest high spots and work your way lower trying to feather your way down. You probably don't want it terraced.

Now for more bad news. This is a poor time of year to seed. It is great for sod but not for seed. Why? Because the grass seed needs continual soil surface moisture for the next few weeks to germinate. So does crabgrass seed. Another reason is the roots on grass seed sprouted now will be unprepared for the summer heat. That is except for crabgrass which has been designed over the eons to sprout in spring and tolerate the summer heat. Sod is the best for use now because it was sprouted last fall (the best time of year for seeding northern grasses).

But here you are and you need to do something. You can wait until fall when it is good to seed and do the entire project then. Or you can do it all now while your hot to do it and take your chances. If you do it now, you will likely need to reseed in the fall anyway because the crabgrass will have pushed out your spring grass. But at least you will have something even if it is crabgrass. If you do a good job seeding in the fall, you do not have to repeat the crabgrass routine every year. As described above, if you do not keep your soil moist all spring, then you will have little to no crabgrass issues next year.

What is the 1,800 square feet area and what is the 2 acres area? Are you only doing the 1,800 square feet?

water deeply and infrequently
Mow at your mower's highest setting
Fertilize on Memorial Day

You'll be surprised at how nice even weeds look when you take care of them.