If there is a lot of weed growth, grass, or debris growing now then a plow and disk would be better. If you can mow it very short first, a tiller at 2 or 3" max would be my choice. Either way I would spray first, as your farmer friend suggested.
IMO a tiller is overkill.
Also think that a tiller makes soft fluffy dirt behind it if done correctly, this will sink in and make ruts as you drive over it if you dont pack it. A disk can leave large clumps if not gone over enough times and still is soft, where your tires will sink and get caught in forrows if not dragged and packed.
You also need to constider how you will pack it? Will you drive your pickup across the landing area, 20 times to pack this soft dirt or will you let it settle out with rain and time and not use it for say a year or more?
IMO a tiller is overkill. You'll waste a lot of time and fuel stirring up several inches of dirt the seed doesn't care about. The disc and drag idea is much better. You will need to run some kind of packer over it after the seed is spread to get good earth-to-seed contact and hope for rain.
Originally the field was very, very rough due to gophers. Last summer I rented a gopher getter and put down poison and that helped. Then an 80 year old gentleman stopped by and asked if he could trap the gophers. I gave him $2 a gopher and the County paid him that, too. He trapped a 190 gophers. Afterwords, I dragged the field and got rid of a lot of the roughness.
I'm going to fly an ultralight off of the field. So I need to be able to travel up to 30 mph with 10 inch tires and not be shaking the ultralight to death.
I just got off the phone with a friend of my dad's and this fellow has been farming the area all his life. He suggested I spray roundup, wait 3 - 5 days then plow with a moldbord plow. Then he said immediately after I should disc. Does that sound like a good plan? Could I get the field as smooth disc'ing and dragging as I could if I used the soil pulverizer/harley rake?