A farmer should only really roll a field no later than March as the ground gets too hard in april to flatten out, also you won't destroy any ground nesting birds nests in March. Normally as a rule of thumb the second week in March is dry enough to roll.
Heavy rolling is used to press down muck flat so it won't get into a forage crop, to press down stones that could damage a mower and to flatten down any mole hills or soil in general that could also get into a forage crop and kill live stock.
Rolling can make grass tiller which in theory should produce more grass. However heavy rolling can knock grasses growth back for a week or so.
Having said that some farmers roll regardless as it looks good and their farther used to do it.
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They rotate their crops to utilize bacteria to increase nitrogen in the soil.
because diffrent crops take up diffrent nutrients so they are rotated to ensure they have a good supply of the right nutrients
they roll grass fields so that tillering can happen which is so that the grass spreads out and it encourages more to grow.