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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. 

Yes, after the lawn is overseeded post-aeration, most of the seed germinates in the aeration holes. This leaves the soil undisturbed while lush and healthy grass will grow in the holes' place. The point of this is to create extra turf density in areas that really need it, such as a large patch of dead grass where a shed used to be.

Aeration is most effective when the soil is slightly moist but not excessively dry or waterlogged. If your lawn's soil is extremely dry, consider watering it a day or two before aeration to facilitate the process. Conversely, avoid aerating when the soil is saturated or excessively wet, as it can lead to poor aeration results and potential damage to your lawn. Finding the right moisture balance is crucial for successful lawn aeration.

Some grass types grow better than others on hard dirt. For example, hardy grass types like perennial ryegrass and Kentucky bluegrass will grow better on tough soil. Keep in mind that you should still consider your area’s climate when deciding on a grass type.