One thing you need to keep in mind is that in your area Mid to late August is the best time to seed. That's because the days are warm and the nights get heavy dews. Great stuff for seeds. if you start pushing the envelope into September it should be before 9/15. I have done the Early October thing and it has mixed results. Ideally seeding in late August will have you mowing the grass before winter (depending on the seed you pick and precipitation you get) which will help it get established better.
About that field, if it is rough, you may well need to plough it, then let it set, cultivate it, disk it, then York Rake or better Harley Rake or Rock Hound the rocks out. I assume you want a finished appearance on it. You can seed it with any rotary type spreader. Make sure you hire someone to blow some straw on if it is a finish lawn you are after

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