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My current lawn used to be a pasture 2 years ago. Needless to say it's bumpy. I want to use my tractor and a pto tiller then level it with drag or device. Question is after this, Do I compact it a little with a weighted roller? Also what time of year is best to do this? Ps. My yard is around 2.5 acres mostly open

In the US, early September is the ideal time to do this. Ideally, you'd like to be able to water but with 2.5 acres this may not be feasible.

A disk would probably work as well or better than the tiller. Disk in at least two directions, maybe more depending on the effectiveness of the disk; fertilize, drag, sow the seed, and drag again. Then you can roll, but you'll probably leave tracks. Seed needs to be in contact with the soil but the combination of dragging and soil that isn't churned into powder makes this happen. The disking and dragging should smooth it out enough that rolling isn't necessary for smoothness.

Then it's up to Mother Nature if you can't water.

Thank you CPuvis, why a disk not a tiller? Also the lawn as it is now is 98% weed free if I disc only the top 5 inches would it not grow back. It's Bermuda. I'm only asking because I assumed it would.

Weeds are going to grow back regardless of which way you break the ground because the seeds are already there. You have to deal with weeds when the grass comes up. Hopefully, it will come up thick enough to crowd out the weeds.

A disk is a lot faster than a tiller but it has to have enough 'umph' to break ground. If you don't have (or can't rent) a tractor and disk that can do this, you'll have to use the tiller. 2 1/2 acres of tilling is a LOT of tilling.

But if your yard is 98% weed-free now, I would not break the ground at all. Just wait until it's good and wet and roll it to smooth it out. Disking or tilling and re-seeding without the ability to water could backfire and you'd end up with a worse stand of grass than you have now. Most people would kill for 98% weed-free yards that size.

Lightening got the tree but you can see its all open but bumpy.

A 3pt hitch tiller will do just fine. In fact I personally think it will do a better job than the disc. A set of old bed springs or a section of chain link fence behind a 4 wheeler or a lawn mower will level it slick.