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What are the pros/cons of aerating in these cooler temps. Here in MA, we're expected to see lows of 29, and highs of 54.

I don’t know about core aeration with regard to temperature. There appears to be two schools of thought on aeration in general, those who oppose it since it can bring up dormant weed seed, and those who swear by it in a positive way. I think the vast majority of people on this site oppose it.