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Hi my name is Brian.
Normally aerating is carried out Spring or Autumn and if you fertilize at the same time it helps the fertilizer get down into the soil and prevents run of when it rains.
But if your soil is very compacted, anytime is good.
if you use a hand held hollow tine aerator or solid tine on a machine Just carry on until your bored.
if your using a hollow tine on a machine one pass should be enough.
I hope this helps you out a little.