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Whether or not grass will fill in bare spots itself depends on the type of grass you have. For example, grass with rhizomes (e.g., Bermuda grass) and stolons (e.g., Saint Augustine grass) will naturally fill in bald spots as it spreads laterally. However, clump-forming grasses will not spread. 

Don't pick up or dispose of aeration plugs. They will break down by themselves in one or two weeks. Rainfall will speed this up, as will watering the lawn. Mowing helps, but don't mow the grass too soon post-aeration. It's unusual that the plugs would remain after three or four weeks, but mowing and raking will break them down by that point.

Aerating a lawn before seeding it or adding new grass seed is a smart decision. By loosening up compact soil and allowing it to take in more air and water, your seeds will have an easier time establishing roots and growing. Aerating beforehand also means your seeds will have better contact with the soil, so more of your seeds have a chance to germinate. If you do plan to aerate your lawn before seeding, aerate about two days before you plan to start seeding.

Overseeding after aeration is not always necessary, but it can be highly beneficial, especially for lawns with thin or patchy areas. Aeration creates an optimal environment for new grass seed germination by improving soil contact and reducing competition from thatch. If you aim to thicken your lawn, address bare spots, or introduce a new grass variety, overseeding immediately after aeration can help rejuvenate and enhance your lawn's overall health and appearance. However, whether you overseed or not depends on your specific lawn goals and condition.