The ability of Bloodthirsty Aerialist triggers just once for each life-gaining event, whether it's 1 life from Impassioned Orator or 4 life from Dawning Angel. If you gain an amount of life "for each" of something or "equal to the number" of something, that life is gained as one event and the ability of Bloodthirsty Aerialist triggers only once.

If Bloodthirsty Aerialist is dealt lethal damage at the same time that you gain life, it won't receive a counter from its ability in time to save it.

Each creature with lifelink dealing combat damage causes a separate life-gaining event. For example, if two creatures you control with lifelink deal combat damage at the same time, Bloodthirsty Aerialist's ability will trigger twice. However, if a single creature you control with lifelink deals combat damage to multiple creatures, players, and/or planeswalkers at the same time (perhaps because it has trample or was blocked by more than one creature), the ability will trigger only once.

In a Two-Headed Giant game, life gained by your teammate won't cause the ability to trigger, even though it caused your team's life total to increase.